TW530050B - Halogenating agents, preparation process of said halogenating agents and process for preparing halogen compounds with said halogenating agents - Google Patents

Abstract

Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.

Description

530050 A7 B7 V. Description of the invention (r η L invention- < i present, VX guest Π P -½ I ea m ^ ^. · Ν · η λ *. ·,-^ L ·. M ηι βί \ M fb m λ: three: two · "two m, mouth! J _ tea 1¾ field] /-: ·. wear $ 4_-person Luguan R 4-U each 4 -.-. fti _ i again zr :: ·: Λ 1. ^ m! B .1! „R .:: 々: r? Rc _predicate

There is a method of Xia ib compound and material _ chemical 乂 b. Generally can be taken _, ϊ f ^; -rV ^ i / * 5l. £ -L -rfc- 丁 十,! / ,,; εΐ. · 'Χ-? ΠΤΠ? IW— U: 1¾' m ^ ~ m 1u " a W 'Country: Tea—Iron ID tT: W /: 1 m X Υ ~ λ · t \ · rf * x ΐ • ^ Λτ * ar— ;, t—ΐ one: two one.— · : ― «· ^ J *-. Rt > r —. —T —i > .ΐ s—: -H ° rtn 5 K] Temple Tetsuya has the genus _ ΐϊ. 毐 枉 5 _fi.: H Most employees of the Central Standards Bureau of the Ministry of Economic Affairs' consumer cooperatives need special equipment and technology to print these tests. Therefore, given that-£-· .//- .. Lr; .- ^ τ- * l · — rr · ^ · —, one:. A ri · *. T ~ 7 i " • 一 r ϊτZZτ ^ x. ~ ； R. Xl ·: f 丄 · ./: · ^: c: ^ ::. — · / \ Zt; * rrr 深 忭 _ 谷 芴 度 、 女 芏 1Ξ. Anti-revolt K > Μ K 合Path Park ID said that the cake% _ exhibition has continued to this day. Especially in the direction of the production of fluorine compounds, fluoride Aγϊ —r 一 --- Xi-: 'zn. Nλ. Ί-t J \ 丄 rt 3ΐ · ν λ -u- nr * ΐ ~-/?疒 ― tm.r zrarr cr? —Λ- * zirr M TO g tS S) B Look;:; Four FG * t day spread happy legs picture ID Han wishing businessmen and soldiers with a high degree of special equipment and technology Wei 5 will also cause a higher economic burden. ~ ； ΊΤΐ ί;-rr ΓΤΊ Λ! Two two f \ Γ ~ ^ Τ TilS ^. ”One £ l: ZT ΙΪ ^ Cit -iX > / ζ £ rr * 1 ^ 7 tn-t dagger, ί " Γ-rr * · Zheng Zheng used the hard id to say "rhyma" and "iti m". The conventional Θ5fluoro_ib agent such as Yang et al. Is toxic, caustic, and in the reaction step 7. ·· * 丄 F Ⅱ: Λ.Ι. ^. R / W * 7- 一 i S XK ^ . r Ί '^ TS on 4-7Tri «-ft f-?-x: Ί ^? .t on .. / b-*' 十 · <: Luo Xu, Zhao Xie, Xie Nan M i 罙 ΐ 卜 5 JE1 Pu Fumu chain mj gx Jian Han 忟 er ° ft: 5 fluorine bonds outside the selectivity in the reaction is poor. On the other hand, in the field of functional materials, physiologically active substances and other various fields, the development of new chemical products using fluorine compounds has been carried out to meet these needs.来 c ^ r? ^ R v- s ^ a: forged limbs m-m i- itr: ~~ industrial products V 1 1 'Γ · *. S ·· factory ： · " ^ r ， guang "s, · Ν 4 ^? A Γχ Λ c ·, ΓΓϊ ^ ----, i ^ TT /? _Two ...- > * 3W * Exhaustion 5 ϋ ί > rd 5 y / 1) 5 t > wi ® I u A 5 ί i. Di 欤 m --- Ethylamine vacancy > is a representative reagent for fluorination of hydroxyl, carboxyl and other oxygen-containing functional groups. It introduces DAST as an excellent fluorinated surface of oxygen in a hydroxyl or carbonyl group. Still, in the preparation of DAST 5

With, — HS rr'5 '七 士 τ * · I ... #-· r \ Jiazhanwanwanshi—f δ-6 0 t, LL. Itb This paper is applicable to China National Standard (CNS) Λ4 specification (210X 297 G 530050 A7 B7 V. Description of the invention () requires special manufacturing equipment. As for safety, U, Fluorine Chem ,, 42 1 37 (1989)] was published in DAST Manufacturing and Explosions in use. In addition, WO 96/04297 shows that tetraalkyl-fluoroformamidine is an excellent fluorinated blue for carboxyl groups. However, no explanation for the fluorination reaction of other functional groups has been issued: The scope of the patent states that the halide ion is included as the counter-ion of the tetraalkyl-fluoroformamidine salt. However, in fact, ρρε- is shown as the only example of the opposite ion. Therefore, the present inventor according to WO 96/04297 The method is to prepare 1,3-dimethyl-2-fluoro_oxazonium iron = hexafluorophosphate, and is used to replace individual hydroxyl groups on benzoic acid, benzyl alcohol and n-octanol with fluorine. As a result, it is generated from benzoic acid. Benzamidine fluorine. However, in the fluorination reaction of benzoic acid and n-octanol, the formation of fluorine compounds cannot be observed. Rishiri Ε I 4-3 0 8 5 3 8 Published the halogenation reaction of the first alcohol using a haloimide iron salt as a halogenating agent. Japanese published patent HE 19-6 7299 describes the halogenation reaction of carboxylic acids. Both of these documents are It is shown that the opposite ion of the iron halide imide includes a halogen ion. However, in fact, the opposite ion is only an example of C 1 _. In particular, no explanation of the fluoride is found. DE 2 6 2 7 9 8 6 and Japanese published patent S Η 0 5 2-1 5 6 8 1 0 illustrate the use of bis-dialkylaminodifluoromethane as a reaction catalyst in the preparation of perfluoroalkoxypropane fluoride. _. However, no description of the fluorinating agent has been issued. This preparation is carried out by reacting hexafluoropropylene oxide with tetraalkylurea, and the source of fluorine is expensive and difficult to handle. As previously mentioned, it has not been developed yet. Oxygen-containing fluorinating agent which is used in industry and is satisfactory in terms of manufacturing method, selectivity, yield and economy. [Invention Summary] This paper standard applies Chinese National Standard (CNS) Λ4 Regulations ( 210 × 297 male f)-5-530050 A7 B7 V. Description of the invention ( The object of the present invention is to provide a halogenating agent, especially a fluorinating agent, which can eliminate the problems of the prior art on the M, and can be produced in the industry by technologically and economically improved methods, and has excellent reactivity and economy. Provide a method for preparing a halogenating agent, and a method for preparing a compound obtained by halogenating a reagent, especially fluorinating various organic compounds. As a result of intensive research done to solve the above-mentioned purpose, the inventors have issued the formula ( 1) The compound represented:

R 1, R Ν

R (1)

X V

Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs where R 1 to R 4 are substituted or unsubstituted, saturated or unsaturated alkyl or substituted or unsubstituted aryl, and they may be the same or different; R 1 And R 2 or R 3 and R 4 may form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or R 1 and R 3 may form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms It is a novel and excellent fluorinating agent with selectivity to hydroxy, carboxyl, formamyl, thiol and other oxygen-containing functional groups, and its application to fluorination does not require special equipment and technology. And it can be performed extremely safely and easily. In addition, it has been found that the compound represented by M chemical formula U) can be prepared via a prime exchange reaction of the compound represented by M chemical formula (14):

R R,, + / Ν

I X 2 X

, R, R (14)-6-This paper size applies to Chinese National Standards (CNS) Λ4 gauge (210X 297 public # 530050 A7 B7 V. Description of the invention (where X 2 and X 3 are chlorine or bromine atoms, and their May be the same or different; R 1 to R 4 are substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted aryl, and they may be the same or different; R 1 and R 2 or R 3 and R 4 can be bonded to form a ring including nitrogen atom or nitrogen atom and other heteroatoms; or β and R 3 can be bonded to form a ring including nitrogen atom or nitrogen atom and other heteroatoms, so no special equipment and technology are required It can also be manufactured safely in industry. It was also found that the fluorinating agent represented by M chemical formula (1) can be recovered in the form of M urea after the fluorination reaction, and can be economically reused as M chemical formula (1 4) The raw material of the compound. In addition, the compound represented by the chemical formula (1 5) was also found: R \ / R 2 / \ R4

R

IX 4 X (15) Printed by the Consumer Standards Cooperative of the Central Bureau of Standards, where X 4 and X 5 are halogen atoms, and except that U and X 5 are fluorine, chlorine or bromine atoms, they may be the same or Different; R 1 to R 4 are substituted or unsubstituted, saturated or unsaturated fluorenyl or substituted or unsubstituted aryl, and they may be the same or different: R 1 and R 2 or R 3 and R 4 may be 鐽It forms a ring including nitrogen atom or nitrogen atom and other heteroatoms. It is an excellent and novel halogenated surface with selectivity to hydroxyl, carboxyl, methyl and other oxygen-containing functional groups, and it is more popular for its application in teeth. The chemical reaction does not require special equipment and technology, and can be performed extremely safely and easily. This paper size applies Chinese National Standard (CNS) Λ4 gauge (210X29? 530050 A7 B7) V. Description of the invention (in other words, the aspect of the invention will be described under U under M) to (45) (1) A M Fluorinating agent represented by chemical formula (1):

R

R

X \ RFF (1) where R 1 to R 4 are substituted or unsubstituted, saturated or unsaturated alkyl, saturated or unsaturated aryl, and they may be the same or different; R 1 and R 2 or R3 and R 4 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or R1 and R3 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. (2) The fluorination in item (1) above M, wherein the fluorinated surface represented by the chemical formula (1) of M is represented by the chemical formula (2) of M; (C H 2) a '

R

N

\ R (2) Printed by the Consumer Standards Cooperative of the Central Bureau of Standards where a is an integer of 2 or 3, and R5 and R6 are substituted or unsubstituted, saturated or unsaturated low carbons with 1 to 6 carbon atoms An alkyl group, and it may be the same or different. (3) The fluorinating agent as described in item (2) above, wherein the fluorinating agent represented by M chemical formula (2) is 2, represented by M chemical formula (3), 2-Difluoro-1,3-dimethyl oxidazolidine: This paper size applies to the Chinese National Standard (CNS) Λ4 specification (210X29H # (Read the precautions on the back before filling this page)

530050 A7 J37 V. Description of the invention (

H3 c—N N—c Η X F

F (3) (4) The fluorinating agent according to item (2) in M above, wherein the fluorinating agent represented by the chemical formula (2) of M is 2, 2 -difluoro-1 represented by the chemical formula (4.) of M , 3 oxazosin: n-butyl η (4) (5) as the fluorinating agent in item (1) above M, wherein the fluorinating agent represented by the chemical formula (1) of the M is the chemical formula (K) of the K:

R \ / R9 > Nr8 / XFF (5) Printed by the Consumer Standards Cooperative of the Central Bureau of Standards, where R 7 to R are substituted or unsubstituted, saturated or unsaturated low carbon with 1 to 6 carbon atoms An alkyl group, and they may be the same or different; R 7 and Η or R 9 and R 1G may be conjugated to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or R 7 and R 9 may be bonded to form a ring including A nitrogen atom or a ring of nitrogen and other heteroatoms. (6) The fluorinating agent according to item (5) of M above, wherein the fluorinating agent represented by the chemical formula (5) of K is bis-dimethylaminodifluoromethane represented by the chemical formula (6) of M: Applicable Chinese National Standard (CNS) Λ4 gauge Taiwan (210 × 297 male f) (Please read the precautions on the back before filling this page)

9 530050 A7 V. Description of the invention (

HsC χ / CH (6)

〉 N N < " H3c / X XCH FF (7) is the fluorinating agent in item (5) on M, wherein the fluorinating agent represented by chemical formula (5) is a double represented by chemical formula (7) of M- Di-n-butylaminodifluoromethane n -H9C4 η -H9C4 -C 4 Η 9 — η

> N N < X

C 4H n (7)

F

FU I p (8) — a method for preparing a fluorine compound represented by M chemical formula (8 -1): (8-1) wherein R 11 is a substituted or unsubstituted alkyl group, and an unsaturated group may be contained therein, It includes a compound having an alcoholic hydroxyl group and represented by K chemical formula (8)

R 11 -0H (8) Printed by the Consumer Cooperative of the Central Standards Bureau of Didi Ministry, where Ru is the same as the chemical formula (8-1) and reacts with the fluorinating agent on M represented by the chemical formula (1) ϋ (9) Preparation method of fluorine compound represented by M chemical formula (9-1): (F) c

Vn < Yl) b (9-1) where Y 1 is an electrophilic substituent, b is an integer from 1 to 5, and c is an integer from 1 to 5 A paper size applies the Chinese National Standard (CNS) Λ4 regulations (210X 297 公 #) 530050

CHF A7 B7 V. Description of the invention () number, and b + c S 6, including compounds of the phenol type or sulfur surface type represented by the chemical formula (9): (QH) (9) where Q is an oxygen or sulfur atom , And Y 1, b, and c are the same as the chemical formula (9-1) and react with the fluorinating agent on M represented by the chemical formula (1). (1 0) — a method for preparing a fluorine compound represented by the chemical formula (1 0-1): (10-1) wherein R 2 is a substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted The substituted aryl group includes an aldehyde compound represented by the chemical formula (10): R 12 -CH0 (10) where R ^ is the same as the chemical formula (] 〇-1), and is represented by KK chemical formula Π), above Reaction of fluorinating agents. (11) A method for preparing a fluorine compound represented by M chemical formula (11 ~ 1): (read the precautions on the back of Λ first, then ^ NΓ page)

R

C line

R 14 / \ f Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs where R 13 and R 14 are substituted or unsubstituted alkyl groups, or substituted or unsubstituted aryl groups, and they may be the same or different; It may include an unsaturated group, and R 13 and R 14 may be bonded to form a ring, which includes a compound represented by the chemical formula (丨 丨):

R

R \ c20 / (11) This paper size applies to Chinese National Standard (CNS) A4 specification (210 × 297 mm) 530050 kl B7 V. Description of the invention (where R and R 4 are the same as chemical formula U 1 -1), and The fluorination reaction of M represented by the chemical formula (1). (1 2) — a method for preparing an acid fluoride represented by the chemical formula (1 2-1): R ^ -C0F (12-1) where R 5 is a substituted or unsubstituted, saturated or unsaturated alkyl group Or a substituted or unsubstituted aryl group, which includes a fluorenyl compound represented by the chemical formula (1 2 :) of M: 15

C00H (12) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs (13) where R0 is the same as the chemical formula (12-1) and reacts with the fluorinating agent on K represented by the chemical formula (1). (13) — A method for preparing a fluorinated hydrazone represented by the chemical formula (13-1): (F) d (13 — 1) where Y1 is an electrophilic substituent, b and d are integers from 1 to 5, and b + dS 6, which includes an aromatic compound containing a halogen atom other than fluorine and represented by the chemical formula (1 3): (X i) d-(YL) b where X i is a halogen atom other than fluorine, and Y 1, ^, and d are the same as the chemical formula (1 3 -1), and react with a fluorinating agent on M represented by the chemical formula (1) ((1 4) a fluorine-containing hydrocarbon compound represented by the chemical formula (2 5) The paper size of the paper is prepared according to the Chinese National Standard (CNS) A4 gauge (210 × 29? Male f) 12-(25) 530050 A7 V. Description of the invention ('R ”RV—〆C — 0 R16

Z wherein R $ to R17 are a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, and they may be the same or different; and Z is-(Y)! 1-CHF2,-(Y) n-CH2F Or -C0-0-(Y) n-CH2F, where Y is -CH2- and η is an integer of 0 or 1 to 5, which includes a fluorinating agent represented by M chemical formula (1) and M chemical formula (2 4) Olefin compound reaction R15 R > = < R16 \ (24)

X wherein R 5 to R 17 is a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms, and they may be the same or different; and X is-(Y) n-CH0,-(Υ) n-CH20H, Or -C 0-0-(Y) η-C Η 2 0 Η, where Y is -C Η 2-and η is 0 or 1 to 5. The number printed by the Consumer Standards Cooperative of the Central Bureau of Standardization of the Ministry of Warping. (1 5) The method according to any one of items 8 to 14 on M is represented by M chemical formula (2). (16) a compound represented by the chemical formula (2): 7 (C H 2) ax wherein the fluorinating agent

R

\ R F F

N (2) where a is an integer of 2 or 3, and R 5 and R 6 are paper sizes of 1 to 6 carbon atoms. Applicable to China National Standard (CNS) A4 regulations (210X297 ^ # 530050 Μ Μ V. Invention Explanation () A substituted or unsubstituted, saturated or unsaturated lower carbon alkyl group, and it may be the same or different. Π 7)-a compound of formula (2), which is represented by the formula 2) Difluoro-1,3-dimethyl_azolidine:

Η 3 C —Ν Ν —C ΗX FF (3) (1 8) —a compound of formula (2), which is 2-difluoro-1, 3-di-n-butyl represented by the formula (4) Oxazolidine: η-Η 9 C 4 —NN—C4 Η Factory η (4) 麴 麴 Read the precautions on the back before writing this page-Pack-Order

FF ί 1 9) A compound of the chemical formula (5), which is a bis-di-n-butylaminodifluoromethane represented by the chemical formula (7) of K: printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs η — Η 9 C 4 Π — Η 9 C 4

> NX FF • C 4 H 9 ~ Π C 4H9-n (7) (2 0) — A method for preparing a fluorinated surface represented by the chemical formula (1) of M in item U) on M, which includes making M Compounds represented by chemical formula (1 4): This paper size applies Chinese National Standard (CNS) A4 regulations (210X297 g) 14 (14) 530050 R 1 to R 4 are substituted or not taken A7 B7 V. Description of the invention （） R1 R3) N '、 + / N 丨 R 2 / XR 4

IX 2 X 3- wherein X 2 and X 3 are chlorine or bromine atomic, saturated or unsaturated alkyl, substituted or unsubstituted aryl, and they may be the same or different; R 1 and R 2 or R 3 and R 4 may be condensed to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or R 1 and R 3 may be condensed to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, and an alkali metal with a fluorine atom The salt is subjected to a halogen exchange reaction in an inert solvent. (2 1) — A method for preparing a fluorinating agent of item (1) on M, which comprises reacting a compound represented by M chemical formula (1 4) with half equivalent of sodium fluoride, separating by filtration, and fluorinating Potassium continues to react. (2 2) — Kind of halogenating agent represented by chemical formula (1 5): Γ Read the notes on the back of Qin before reading this page)-Pack · R 1

R

N

, R R (15)

X 4 X Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs where X 4 and X 5 are halogen atoms, except that X 4 and X 5 are fluorine, chlorine or bromine atoms * they may be the same or different; R 1 To R4 is a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, which may be the same or different; R 1 and R 2 or R 3 and R 4 may be bonded to form including A nitrogen atom or a ring of a nitrogen atom and other heteroatoms; or R1 and R3 may be linked to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. (23) The halogenating agent according to item (22) of M above, wherein the halogenated surface represented by chemical formula (15) of M is represented by chemical formula (16) of K: This paper size is applicable to Chinese National Standard (CNS) Λ4 specification (210X2W)蝥 1 Γ: 530050 A7 137 V. Description of the invention ((CH 2) a '

\ R X4 X (16) where 5U and X 5 are halogen atoms, except that X 4 and X 5 are fluorine atom, chlorine atom or bromine atom, which may be the same or different; a is an integer of 2 or 3, R 5 and R 6 are substituted or unsubstituted, saturated or unsaturated lower carbon alkyl groups having 1 to 6 carbon atoms, and they may be the same or different. (2 4) The chemical reagent of item (2 3) above, wherein the halogenated halogen represented by the chemical formula (1 6) is a 2-pyridyl-1, 3 -dimethyl group represented by the chemical formula (17) Oxazoline_ = halide: H3 C—N +. N—C Η (17) X4 Xs 'Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Lithium where X 4 and X 5 are halogen atoms, except U) and ) (5 are all except fluorine atom, chlorine atom or bromine atom, which may be the same or different. (2 5) The halogenating agent according to item (2 3) above, wherein the halogenation represented by the chemical formula (1 6) of M Agent is 2-fluoro-1, 3-dimethylimidazolium represented by chemical formula (1 8) = chloride: H3 c—N, + · Ν—C Η (18)

FC This paper size applies to Chinese National Standards (CNS) Λ4 gauge (210 × 297 public # # 16-530050 A7 B7 V. Description of the invention ((2 6) As the amylating agent in item (2 3) on M, where the K Halogenating agent meter represented by chemical formula U 6) 2_fluoro-1,3-dimethyloxazoline iron = bromide represented by chemical formula (19): H3 C—N +. Ν—C Η 3 (19) FB r (2 7) is a halogenating agent according to item (2 3) above, wherein the halogenating agent represented by the chemical formula (1 6) is 2-fluoro-1, 3-dimethyl represented by the chemical formula (20) Imidazolium iron iodide: H3 C—Ν Ν—C Η (20) (Please read the notes on the back of Christine before writing this page)

F The halogenated agent printed by (2 8) such as the item (2 3) on the M is printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Dishes, where the chemical agent represented by the chemical formula Π 6) is a chemical agent represented by the chemical formula M (21) 2 -Chloro-1,3-dimethylimidazolium 啭 鏺 = bromide:

Hs C-N N-CH (21)

CB r (2 9) is a halogenating agent according to item (2 3) above, wherein the chemical surface represented by the chemical formula U 6) is 2-chloro-1, 3-dimethyl represented by the chemical formula (22) _The paper size is applicable to Chinese National Standards (CNS) Α4 gauge (210 × 297 公 # # 17 530050 A7 B7 V. Description of the invention (啭 钂 = Iodide (22)

H3 C-N N-CH

C (3 0) The halogenating agent according to item (2 3) in M above, wherein the halogenating agent represented by the chemical formula (1 6.) Is 2-iodo-1,3-dimethyl represented by the chemical formula (23). Oxazoline 钂 = iodide; (23)

Ha c—N t +; N—CH (3 1) A method for preparing a halogenating agent represented by 丨 y and the above chemical formula (1 5) as item (2 1) on M, which includes the formula (1 4) Compounds represented:

R., I NR 2 /

.R R (14) Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs

Χ2 X wherein X ^ RX3 is a chlorine or bromine atom, and R1 to R4 are the same as those of M, and are halogen-exchanged with a fluorine atom, a chlorine atom, a bromine atom, or an iodine alkali metal salt or a mixture thereof in a sensitive solvent. (3 2) — a method for preparing a halogen compound represented by the chemical formula (8 -2) (8-2) wherein R u is a substituted or unsubstituted alkyl group, and it may contain an unsaturated paper. Standard (CNS) Λ4 regulation (210X29D &#;# 18-530050 A7 B7 V. Description of the invention () and group, and X 5 is a _ atom, which includes an alcoholic hydroxyl compound represented by the chemical formula (8): 11 0Η ( 8) wherein R Μ is the same as the chemical formula (: 8-2.), And reacts with the halogenated surface on K represented by the chemical formula (1 5):

R〉 N,,. 丨, N ((15)

/ \ R χ. X 6 ·· where) U, X 5, and R 1 to R 4 are the same on M. (33) A method for preparing an acid halide represented by M chemical formula (1 2-2): 15

C0X (12-2) Printed by the Consumer Standards Cooperative of the Central Bureau of Standards, where R @ is substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted aryl, and X e is The halogen atom represented by X 4 or X 5 in the chemical formula (1 5) includes a carboxylic acid compound represented by the chemical formula (1 2): R 15 — C 0 0 Η (12) wherein R% is the same as the chemical formula (1 2-2 丨 is the same, and reacts with the halogenated surface represented by M chemical formula (1 5): R 1

R

, R R (15)

X 4 X This paper size applies Chinese National Standard (CNS) Λ4 gauge (210X297 male f) 19 530050 A7 B7 V. Description of the invention () Among them, U, X 5 and R 1 to R 4 are the same as those on M. (3 4) —Method for preparing a fluorine compound represented by M chemical formula (10-2): R 12-CH (X 7) 2 (1 0-2) where R 12 is substituted or unsubstituted, saturated or unsubstituted A saturated alkyl group, or a substituted or unsubstituted aryl group, and X 7 is X% or a halogen atom represented by X 5 in the chemical formula (1 5), and two X 7 may be the same or different, including The aldehyde compound represented by (1 0): R 12 -CH0 (10) where r η is the same as the chemical formula (10-2) and reacts with the halogenating agent represented by the chemical formula (15): (Read the note on the back first Matters refill this page-Pack · R 1

R >,

R (15)

, 1T

X 4 X Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Yield, where X 4, X 5 and R 1 to R 4 are the same as K Shang. (3 5) The method for producing a halogen compound according to any one of items 32 to 34 above, wherein the halogenating agent is represented by the chemical formula (1 7) of M. (3 6) — a compound represented by M chemical formula (1 5):

RX 4 χ5 · (15) where X 4 and X 5 are halogen atoms, except that X 4 and X 5 are fluorine atom, chlorine atom or bromine atom, which may be the same or different; R 1 and R 4 are substituted Or this paper standard applies Chinese National Standard (CNS) Λ4 gauge (210 × 29 < M > §) 20 530050 A7 B7 V. Description of invention () Substituted, saturated or unsaturated alkyl, or substituted or unsubstituted aromatic And they may be the same or different; R 1 and R 2 or R 3 and R 4 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or R 1 and R 3 may be bonded to form Including nitrogen or nitrogen and other heteroatoms. (3 7) — a compound represented by the chemical formula (1 6): (C H 2) a,

R

N

\ R (16) (_Read the precautions on the back first, then _write this page

x4 X except that X 4 and X 5 are each a fluorine atom, a chlorine atom, or a bromine atom, X 4 and X 5 are the same or different halogen atoms, a is an integer of 2 or 3, and R & and R 6 are A substituted or unsubstituted, saturated or unsaturated lower carbon alkyl group having 1 to 6 carbon atoms, and they may be the same or different. (3 8) A halogenating agent such as the item (2 2) on M, wherein the halogenation is referred to as 2-halo-1,3-dimethyl_oxazoline iron represented by M chemical formula Π 7) = halide ： Order H a C—N Ν —C Η 3 Printed by the Consumer Cooperative of the Central Standards Bureau of Didi Ministry (17) χ4 X 5 which is the same as that on K (3 9) — a compound represented by the chemical formula (1 8) of M Juki_Zirconium Iron Zeta Chloride: A paper size applicable to Chinese National Standard (CNS) Λ4 gauge (210 × 297 ^ # 21 530050 A7 B7 V. Description of the invention (Η 3 C —N + · Ν —C Η (18 )

FC ί 4 0) — a kind of compound represented by the chemical formula (1 9) oxazolyl = bromide: fluorine-1, 3-dimethylfluorene 3 C—N; Ν—C Η (19) FB r (41 ) A compound represented by the chemical formula (20), 2-fluoro-1,3-dimethyl_oxazole = iodide: Η 3 C-N + · Ν—C Η (20)

FU 2) — a compound represented by the chemical formula (2 1), 2-chloro-1, 3 -dimethyl_sialo_ = bromide: printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Distillation 3 C —N , +; Ν 一 C Η (21)

CB r (4 3) — a compound represented by the chemical formula (2 2) based on oxazolyl bell = iodide: -chlorine-1, 3-dimethyl This paper applies the Chinese National Standard (CNS) Λ4 gauge ( 210X29? F) 22 530050 Printed by the Consumers Cooperative of the Central Standards Bureau of Didi Ministry

Η 3 C —N +, N —C H (22)

C (44) A compound represented by the chemical formula (23): oxazolyl iron = iodide: Η 3 C —N, +, N —C Η 2 -iodine-1,3-dimethyl (23) 4 5) — A method for preparing a halogenating agent represented by the chemical formula (1 5): R \ / R3 r2 / \ r4 IX 4 χ5-(15) wherein R 1 to R 4 are the same as those on the M, which includes the chemical formula U The combination of expressions_ * R 3

Rl> N &lt; R2 / X XR F F (1) wherein R 1 to R 4 are the same as those of · W, and are subjected to a halogen exchange reaction with an alkali metal salt of a chlorine, bromine or iodine atom in the presence of an inert solvent. The halogenating agent of the present invention, especially a fluorinating agent, a fluorinating agent of a hydroxyl group, a carboxyl group, and other oxygen-containing functional groups of the compound, can be safely and easily operated, and has high selectivity. The preparation of the fluorinated surface of the present invention does not require special equipment and the paper size is applicable to the Chinese National Standard (CNS) Λ4 specification (210X 297 male f -23-530050) printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs. () Technology can be carried out economically. In addition, halogenating agents prepared by replacing halogen atoms with other halogen atoms can also be used to prepare compounds with halogens other than fluorine. 0 The halogenating agent of the present invention, especially a fluorinating agent There is no problem with the conventional technology of preparing the reagent itself in the industry, and it exhibits excellent effects as an organic compound, especially a halogenating agent having an oxygen-containing functional group, especially a fluorinating agent. [Simplified description of the diagram] Xian 1 is the IR spectrum of 2, 2-difluoro-1, 3-dimethyloxazolidine prepared in Example 1. [Detailed description of the invention] The fluorinating agent will be described. The fluorine of the present invention The chemical agent is a compound represented by the chemical formula (1) on M: Ri R3> Ν Ν <R 2 / \ R 4 ⑴ FF where R 1 to R 4 are the same as those on K. In the chemical formula (1), R 1 to R 4 Respectively substituted or unsubstituted, saturated or Unsaturated alkyl, or substituted or unsubstituted aryl, and they may be the same or different [R 1 and R 2 or R 3 and R 4 may be combined to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms Or 1 and R 3 may be combined to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. R1 to 1 ^ 4 are preferably an alkyl group or an aryl group having 1 to 6 carbon atoms. The alkyl group may be Straight chain or branch key This paper standard is applicable to Chinese National Standard (CNS) Λ4 gauge (210X297 male) 〇, (· Please read the precautions on the back page first) 丨 Installation ·? --Line 530050 kl B7 Ministry of Economy Printed by the Consumer Standards Cooperative of the Central Bureau of Standards 5. Description of the invention () 1 1 I Dan includes methyl ·, ethyl Λ n-propyl, allyl isopropyl, n-butyl 1 1 1 ', butenyl and n-hexyl Group 0 aryl includes benzene: group 0 β ί to R4 may be the same or not 1 I ί 1 I the same 〇 1 See also 1 R 1 and R 2 or R 3 and R 4-may be individually linked to form a nitrogen-containing proton 1 I atom and a hybrid BU having 3 to 5 carbon atoms. For example, a pyrrolidine ring and, ν .. Note of hydrogen 1 I means 1 I pyridine ring. Item rS_ 1 1 Furthermore, R 1 and R 3 may be鐽 结 形 ®; a 5- or 6-membered ring containing two nitrogen atoms in the ring, such as 5 Of oxazolone ma m, m oxazolone ftol pyrimidine ring, and m page 1 I pyridine II ring 〇1 1 Examples of chemical formula (1) represented by I M and used in the present invention are preferred fluorinating agents. Examples include the following chemical compounds: 0 m 4 \ Λ. However, the scope of the present invention is not limited to iy. The compound shown below is an example of a compound. I bisdimethylamino-difluoromethane Λbis-diethylamino-difluoromethane • V bis-1 1 I bis-n-propylamino- —-, Fluoromethyl bis-di-isopropylamino-difluoromethane ', bis- 4 1, linear bis-propylpropylamino-difluoromethyl synthesis &gt; bis-di-n-butylamino-difluoromethyl synthesis , 1 1 1 di-n-hexylamino-difluoromethyl> bis- (1-pyrrolidinyl) -difluoromethane, bis 1 I — (1-• hexahydropyridyl) -difluoromethyl ATC, 2, 2 -£ i..y-^ -1, 3-dimethyl_azole 1 I 2, 2-difluoro-1,2 Ϊ-diethyloxazoline ·, 2, 2 difluoro-1, 3- • di-n-propanyl 1 1 oxazodine, 2, 2-difluoro-1,3-diisopropyloxazodine, 2: 2: 2-: difluoro-1, 1 1 Q one-two return Propyl_oxazole 2,2- • difluoro-1,3; -di-n-butyl_azolidine, bis (1 1 N- -methyl-N-phenyl) difluoromethane, 2,2 a ~ &quot; Fluoro-1,3 dimethyl_azolidine-1 1 I 4, 5--di_, 2 s 2--difluoro-1,3嗣, and 1 I 2, '2- -difluoro-]., Ξ! ~-Di ＋ P-based pyrimidine 〇1 1 This paper size applies to China National Standard (CNS) M · Jingjing — 530050 A 7 [Π V. Description of the invention () A particularly good test surface is 2,2-difluoro-1,3-dimethyl-oxazole, represented by chemical formula (3), and 2y2 -difluoro-1, represented by chemical formula (4). , 3-di-n-butyl-oxazolyl Bis-dimethylamino-difluoromethane represented by the chemical formula (6), and bis-di-n-butylamino-difluoromethane represented by the chemical formula (7). In the present invention, the fluorinated surface represented by the chemical formula M) can be prepared by the following method. In other words, let the compound represented by the chemical formula (1 4): R1 / / R3 r 2 / \ R 4 (14)

I X2 X 3 ~ Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economics where X 2 and X 3 are chlorine or bromine atoms, and they may be the same or different; R 1 to R 4 are substituted or unsubstituted, saturated or not A saturated alkyl group, or a substituted or unsubstituted aryl group, which may be the same or different: R 1 and R 2 or R 3 and R 4 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; Or R 1 and R 3 may be condensed to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms, and a halogen exchange reaction with an alkali metal salt of fluorine in an inert solvent. This fluorinating agent can be easily and safely prepared. The alkali metal salts of fluorides that can be used are fluorinated planes, gadolinium fluoride, potassium fluoride, and sodium fluoride. The preferred alkali metal salt of fluoride is spray-dried potassium fluoride used in the fluorination reaction. This grade is advantageous in terms of economics and reaction efficiency. The chemical formula (14) is usually a chlorine atom. However, compounds having a bromine atom of X 2 and X 3 may also be used. 2 6 The actual compounds include tetraalkyl-chloromethanthane = chloride, 2-chlorine. The paper size applies the Chinese National Standard (CNS) Λ4 regulation (210 × 297 male f) 530050 A7. B7 V. Description of the invention () 3 -Dialkyl __ = chloride, tetraalkylbromoformamidine_ = bromide, and 2-bromo-1,3-dialkyl-iron = iron = bromide, used as a halogenating agent such as phosgene, Thiophosphine, thionine bromide, phosphorus trichloride, or phosphorus tribromide to prepare compounds represented by Chemical Formula Π) Chemical Formula Π 4) Compounds include, for example, tetraalkylurea, tetraalkyl Thiourea, N, -dialkyloxazolidine or N, fT-dialkyloxazole sulfur S. For example, $ 2-chloro-1,3-dimethyl-oxazodine iron = chloride can be easily prepared by the method described in Japanese Laid-Open Patent SH0 59-25 3 75. Actually, a solution of chloramphenicol dissolved in carbon tetrachloride was added dropwise to 1,3-dimethyl-oxazolidinone, and reacted at a temperature from room temperature to 60 t! For several hours to several tens of hours. In preparing the fluorinating agent represented by the chemical formula (1) of M in the present invention, the amount of the alkali metal salt of fluorine used in the halogen exchange reaction is two equivalents of tetraalkyl-haloformamide = the amount of halide. Good, 2 to 5 equivalents are better. An amount below 2 equivalents will not change the halide. On the other hand, an amount exceeding 5 equivalents does not significantly improve the reaction yield. Printed by the Consumer Cooperative of the Central Standards Bureau of Didi Ministry. There is no special restriction on the solvents used in the halogen exchange reaction, as long as the solvents do not react with the tetraalkyl-halomethyl iron = halides and the compounds produced. The preferred solvents include ethyl methylformamide, 1,3-dimethyl-2-azolidine, dichloromethane and dichloroethane. The amount of dissolved surface in the reaction is not particularly limited. However, from the standpoint of reaction efficiency and ease of operation, its amount is preferably 1 to 10 times the weight of the reaction substance. From the viewpoint of the reaction speed and the stability of the produced products, the reaction temperature is 2 7 This paper size is applicable to the Chinese National Standard (CNS) Λ4 specification (210 × 297 public #) 530050 A7 5. The description of the invention () is in the range of -20 to In the range of 1501, M0 to 10〇υ is more preferable. The halogen exchange reaction for preparing the fluorinated compound of the present invention can also be carried out in the presence of a phase transfer catalyst such as a fourth mirror salt or a fourth alkylphosphonium salt. The reaction mixture of the halogen exchange reaction can be used intact for the next fluorination reaction, or it can be used in the next halogenation reaction after filtering out the organic salt and distilling off the reaction solvent. The reaction product can also be isolated and used by distillation. The fluorination reaction using the fluorinating agent of the present invention can be performed extremely easily using ordinary reaction equipment. For example, the fluorination of a carboxylic acid can be performed simply by adding a carboxylic acid to a reaction mixture of a halogen exchange reaction and reacting at room temperature for several hours. Related fluorides of carboxylic acid compounds can be prepared in such a high yield. The fluorination reaction of the alcohol species can also be performed by directly adding the alcohol compound to the reaction substance of the halogen exchange reaction and reacting for several hours. Relevant fluorides can be produced in high yields. The fluorination reaction using the fluorinating agent of the present invention will be described in detail below. (1) Conventionally, the general and compelling method for the direct conversion of alcoholic hydroxyl groups into fluoro groups in the synthesis of monofluoro compounds. Ϋ Printed by the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Lithography, which can be effectively used for conversion reactions. Representative fluorinating agents include hydrogen fluoride as an acid agent, hydrazone- (HF) η, fluoroalkylamines (Yarovenks reagent), diethylamine-hexafluoropropane adducts ( M is abbreviated as PPDA), SF 4 (tetravalent sulfur compound), trifluorodiethylaminosulfur (D abbreviated as DAST hereinafter), and Ph PF 4 (pentavalent phosphorus compound). As previously mentioned, hydrogen fluoride is difficult to handle due to toxicity, corrosiveness, and the danger of explosion during the reaction step, and it requires the disadvantages of special equipment and technology. This paper standard applies to Chinese National Standards (CNS) Λ4 specifications (210 × 297 公 # ) 0 0 530050 A7 B7 V. Description of the invention (). Guanpu- (ΗP i η) has a higher fluorinating ability than hydrogen fluoride itself. However, this ability is not as high as other fluorinating agents. Yalofan reagent: Fluoroalkylamine is added to diethylamine to A fluorinating agent made from chlorotrifluoroethylene. This reagent can fluorinate a variety of first and second alcohols under mild conditions in a solvent. However, the stability of this reagent itself is low (may be in a sealed, shady Place kept for several days) [J * Gen Che. USSR 1 9, 2125 (1959) 1 〇 PPDA is more commonly used because it is more stable, easy to handle, and has similar reactivity. Recently, Ν, Ν- Diisopropyl-2-fluoroenamine was published as a novel type of fluoroamine-based fluorinating agent [Tetrahedron Lett ,, 30, 3077 (1989)]. These agents are effective fluorinating agents for alcoholic hydroxyl groups. However, by From the complicated synthetic steps and economic point of view, it is difficult to practically apply it to industrial regulations. In addition, DAS T also has similar problems in the substitution of alcoholic hydroxyl groups by M fluorine groups. The fluorination of the present invention can be described as It is safe and easy to operate, and provides fluorinated substances with high selectivity. The problem of the conventional fluorinating agent in the fluorination reaction of alcoholic hydroxyl groups printed by industrial and consumer cooperatives can be eliminated by using the fluorinating agent of the present invention. The method for preparing a fluorine compound from an alcoholic hydroxyl compound using the fluorination difficulty of the present invention is as follows In other words, make the alcoholic hydroxyl compound represented by the chemical formula (8) of M: R 11 -0Η (8) wherein R η is the same as above and reacts with the fluorinating agent of the present invention, and the paper size of the paper is adapted to Chinese national standards ( CNS) Λ4 gauge (210 × 297 公 #) ^ 0 530050 A7 B7 V. Description of the invention () Fluorine compound represented by M fb formula (8 -1): R 11 -F (8-1) where R u is Identical to M. Representative alcohol compounds having hydroxyl groups that can be fluorinated include, for example, methanol, ethanol, n-propanol, n-butyrate, isobutanol, 2-methyl-1-butanol, n-pentyl Alcohol, neopentyl alcohol, isopentyl alcohol, n-hexanol, 2-methyl-1-pentanol, 2-ethyl-1-butanol, n-heptanol, n-octanol, 2-ethylhexanol, n-nonyl alcohol Alcohol, 3,5, 5 to trimethyl-1 -hexanol, n-decanol, n-undecanol, n-dodecanol, allyl alcohol, methylpropanol, crotyl alcohol, benzyl , Phenethanol, cinnamon alcohol, 2-propynol, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, and other first alcohols; isopropanol, second butanol, second pentanol, second Isoamyl alcohol, 1-ethyl-1-propanol, 4-methyl-2-pentanol, 1-methylhexanol, 1-ethylpentanol, 1-methylheptanol, cyclohexanol, 2 -Methylcyclohexanol, 3-methylcyclohexanol, 4-methylcyclohexanol, second phenylethanol and other second alcohols; and third butanol, third pentanol, and 1 -methylcyclohexanol Alcohols, a-pinols, and other tertiary alcohols. However, the kind of alcohol is not limited to these compounds. Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs These M-formulas (8) can be individually provided with the corresponding alkyl fluorides represented by the M-formula (8 -1). The amount of fluorinating agent to alcoholic hydroxyl group is usually 1 equivalent M. The hydrogen fluoride generated in the reaction can be captured using a base such as a third amine. The reaction solvent is not particularly limited as long as the solvent does not react with the fluorinated solvent and the fluorine compound produced by the fluorinated alcohol. The preferred solvents are ethyl acetate, dichloromethane, dichloroethane, dimethylformamide, and 1,3-dimethyl-2 -__ pyridine_. This paper scale applies Chinese National Standard (CNS) Λ4 specification (210 × 297 male 1) 0 Λ 530050 A7 B7 V. Description of the invention Depending on the nature of the reaction, and from the viewpoint of the reaction rate and the stability of tetraalkylfluoromethylamine-fluoride, it is usually in the range of -40 to 1 0 &quot; C, M-2 0 to 8 0 ° C is preferredϋ When the fluorine compound produced has a low boiling point or a structure that easily releases hydrogen fluoride, the reaction temperature needs to be as low as possible. The fluorine compound produced by the reaction can be easily mixed from the reaction by distillation or other methods (2)-It is generally believed that the conversion of phenolic hydroxyl groups into fluorine groups can be achieved through the application of conventional fluorinating agents such as hydrogen fluoride, pyridine- (HF) η, fluoroalkylamines (Yalofan Test Class I ), PPDA, SF 4 (tetravalent sulfur compound), DAS T, and Ph PF 4 (pentavalent phosphorus compound). However, no examples of applying these fluorinated surfaces to such conversion reactions have been found. Even These fluorinating agents can be applied and will still occur in the reaction The same problem of fluorene. The fluorinated surface of the present invention can also be advantageously used for the fluorination reaction of fluorene hydroxyl groups. The fluorination reaction of sulfur can also be performed. However, this reaction is easily accompanied by the formation of disulfide compounds_ as a by-product. The fluorination reaction of phenolic hydroxyl group can introduce an aromatic fluorine compound by selectively introducing fluorine atoms into the aromatic ring. The reaction method is as follows. In other words, the phenol compound or sulfur compound represented by the chemical formula (9) is used. : (QH) c-(Y ^ b (9) wherein Q, Y 1, b, and e are the same as those on M and react with the fluorinating agent of the present invention to prepare a fluorination represented by the chemical formula (9-1) _Compounds: This paper is in accordance with Chinese National Standards (CNS) Λ4 Regulations (210 × 297 Public Dream 3 1 — (Please read the precautions on the back before filling in this page.)--530050 A7 B7 V. Description of the invention (( F) c where γ- (YOb (9-1)) b and c are the same as the chemical formula (9) and can be fluorinated compounds having one or more electrophilic substituents such as -N 0 -CN, -CF 3, -C Η 0--COO Η &gt; and -C 0-〇 Preferred Consumer Cooperatives of the Central Standards Bureau of Didi Ministry The produced phenolic compounds include, for example, o-nitrophenol, p-nitrogen, o-cyanophenol, p-fluorophenol, p-hydroxybenzaldehyde, o-hydroxybenzaldehyde, p-hydroxytrifluoromethylbenzene, _hydroxytrifluoromethylbenzene, Methyl hydroxybenzoate, methyl o-hydroxybenzoate, 4,4 ^ dihydroxybenzophenone, p-hydroxybenzoic acid, o-nitrothiophenol and p-nitrothiothione However, phenol and thiophenol compounds are not It is limited to these compounds. These ® or thiophenol compounds represented by M chemical formula (9) provide corresponding fluorine compounds represented by M chemical formula (9-1). The amount of fluorinated surface hydroxyl groups is usually 1 equivalent M. The hydrogen fluoride generated in the reaction can be captured by a base such as a third amine. The reaction solvent is not particularly limited, as long as the solvent does not react with the fluorinated surface and the fluorine compound produced by the fluorinated phenol '. The preferred solvents are acetonitrile, dichloromethane, dichloroethane, dimethylformamide, and 1 f 3 -dimethyl-2 -oxo spray. The reaction temperature depends on the reactivity of the dissolving surface and the hydroxyl group, and is usually from -0 to 150 ° from the viewpoint of the degree of stability of the reaction and the stability of the tetraalkylfluoromethylamine _ == fluoride. Within the range of C, M 2 0 to 110 ° C is preferred. The fluorinated compounds produced by the reaction can be easily self-remixed by distillation (please read the precautions on the back before filling this page) r equipment · This paper size applies to Chinese National Standard (CNS) Λ4 specification (210X 297 male f) 3 2 Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 530050 A7 B7 V. Description of the invention () The compound is separated. (3) The direct conversion of formamyloxy to a fluorine group is also a monthly method for the preparation of fluorine compounds. Regarding the direct fluorination of formamyl or oxo carbonyl, in the fluorinated surface on M, SF41DAST is known. However, these fluorinating agents are not satisfactory because of the severe restrictions of the former. The fluorinated surface of the present invention can effectively achieve the fluorination of the group. The method is as follows. In other words, make the aldehyde compound represented by the chemical formula (1 0) of K: R 12 -CH0 (10) where R ί 2 is a substituted or unsubstituted, saturated or unsaturated alkyl group, or a substituted or unsubstituted aryl group, and The fluorinating agent of the present invention reacts to prepare, for example, a fluorine compound represented by the chemical formula (1 0-1): R 12 -CHF2 (10-1) wherein R 2 is the same as the chemical formula Π 0). Therefore, the direct fluorination of Φsakyloxy can be effectively achieved by using the fluorinating agent of the present invention. Examples of compounds having fluorinable methylsalyl include, for example, formaldehyde, acetaldehyde, acrolein, methacryl, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, hexanal, and heptaldehyde , Octaldehyde, nonanal, decanal, and other aliphatic aldehydes; cyclohexanecarboxaldehyde and other alicyclic aldehydes; benzaldehyde, p-nitrobenzaldehyde, p-methoxybenzaldehyde, phthalaldehyde, 1-naphthaldehyde, and Other aromatic aldehydes; and nicotinic aldehyde, furan formaldehyde, and other heterocyclic aldehydes. However, aldehydes are not limited to these compounds. This paper size applies the Chinese National Standard (CNS) Λ4 specification (210 × 297297 ##) (read the precautions on the back before filling this page) r_ 530050 A7 B7 V. Description of the invention () Can be made corresponding to this Fluorinated lions such as aldehyde compounds and having the chemical formula (10-1). The amount of the fluorinating agent to the methyl group is preferably 1 equivalent M. The reaction solvent is not particularly limited as long as the solvent does not react with the fluorinating agent, the methyl compound, and the reaction product. The preferred solvents are acetonitrile, dichloromethane, chloroform, dichloroethane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, N-methylpyrrolidine, and dimethylformamide. Satamine and 1,3-dimethyl-2-_azolidine_. The reaction temperature M is preferably in the range of 0 to 150 ° C, and more preferably 20 to 110 ° C. The fluorine compound produced by the reaction can be easily separated from the reaction mixture by distillation. In addition, bis-dialkylaminodifluoromethane can be recovered in the form of K-tetraalkylurea after the reaction is completed. (4) In the preparation of fluoride fluoride, it is a very useful method when the method for directly converting oxygen to fluorine is effective. In other words, make a fluorene compound having a keto group and represented by the chemical formula (Η); (Read the precautions on the back before filling in this page

, 1T

Printed by the Consumers' Cooperative of the Central Standards Bureau of Didi Ministry, where R ί3 and R μ are the same as those on M and react with the fluorinating agent of the present invention to prepare a fluorine compound represented by the chemical formula (-1 -1):

Rl3 \ / F \ C ((11-1)

K 1 4 / \ F where R ί3 and R 14 are the same as on M. Any compound with a fluorene group in the molecule can be used in the fluorination reaction. The paper size is applicable to the Chinese National Standard (CNS) Λ4 gauge (210X29D &gt; ft) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 530050 A7 B7 5. Description of the invention () As _ compound. Such ketone compounds are, for example, aryl ketone compounds and alkyl compounds. However, there are no restrictions on these compounds. The amount of bis-dialkylaminodifluoromethane as a fluorinating agent to ketone is 1 equivalent. M. There is no particular limitation on the solvent used in the reaction, as long as the solvent does not react with the fluorinating agent, ketone compound and reaction. The product can be reacted. Preferred solvents are ethyl alcohol, dichloromethane, chloroform, dichloroethane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, N-methylpyrrolidone, and dimethylformamidine. Amine and 1,3-dimethyl-2 -oxazolyl. The reaction temperature M is preferably in the range of 0 to 150 ° C, and more preferably 20 to Η0 ° C. The fluorine compound formed by the reaction can be easily separated from the reaction mixture by distillation. After the reaction is completed, the fluorinated M can be recovered as the relative urea compound. (5)-Generally use fluorinated benzophenone prepared by the fluorination reaction of benzophenone, a compound of fluorene, as the material of polyether ether and other polyether resins. Polyether ether is a super engineering plastic with excellent heat resistance, electrical insulation, sliding properties and chemical resistance. Fluorinated benzamidine is also used as a raw material or intermediate product for flame retardants, analgesics, platelet coagulation inhibitors, and thrombosis inhibitors, so it is an important compound in the fields of medicine and agricultural chemicals. The fluorinating agent of the present invention can directly fluorinate the hydroxyl group of the hydroxy dibenzyl surface represented by the chemical formula below: (Read the precautions on the back before filling in this page

, 1T 〇

II r

530050 Α7 Β7 V. Description of the invention

(F) m

&lt; F) Printed by the Consumer Cooperatives of the Central Bureau of Standards, Ministry of Economic Affairs, where m and rr are the same as those on M. The hydroxy-substituted benzamidine used in this method can be 2-hydroxydibenzophenone, 4-hydroxydibenzidine, and others having any one selected from 2-hydroxyphenyl, 4-hydroxyphenyl, 2 , Two 4-benzyl derivatives of 2,4-dihydroxyphenyl, 2,5-dihydroxyphenyl, 2,6-dihydroxyphenyl and 2,4,6-trihydroxyphenyl. The amount of the fluorinating agent for the hydroxyl group is preferably 1 equivalent M, and from the standpoint of the reaction efficiency of the unreacted hydroxyl group when using less than 1 equivalent, it is desirably 1 to 10 equivalents. There is no special account for the solvents used in the reaction, as long as the solvent does not react with the fluorinating agent, the dibenzophenone compound substituted with a hydroxyl group, the reaction product, and the dibenzophenone compound substituted with fluorine. Preferable solvent-soluble solvents [Ethyl W, dichloromethane, chloroform, dichloroethane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, N-methylpyrrolidine surface, N, N-di Methylmethanamine and 1, 3 -dimethyl-2-0 mizolidine. The reaction temperature M is preferably in the range of 0 to 15010, and more preferably 20 to 1101. When the temperature is lower than 01, the reaction speed becomes low, and complicated procedures are required. Exceeding the reaction temperature will reduce the stability of the fluoride, and it is alive (Please read the precautions on the back before filling this page

， 1T This paper size applies Chinese National Standards (CNS) Λ4 Regulations (210χ 297 公 # 3 8 Printed by the Consumer Standards Cooperative of the Central Standards Bureau of Didi Ministry. This paper standards apply Chinese National Standards (CNS) Λ4 Regulations (210χ 297 F) 530050 kl V. Description of the invention () Tendency to form by-products with difluorinated radicals. However, phenyl difluorocarbon substituted with difluoride can be easily restored to be substituted with fluorine by hydrolysis. Benzene_. The fluorine compound produced by the reaction can be easily separated from the reaction mixture through distillation, extraction and other steps. After the reaction is completed, the fluoride used can be recovered in the form of urea. (6) Conventionally, the fluorinating agent used in the conversion reaction of carboxylic acid to fluorinated carbonyl group is SF # tetravalent sulfur compound and trifluorodiethylaminosulfur (hereinafter referred to as DAST). SF 4 can directly convert fluorenyl group Into trifluoromethyl. However, this conversion reaction has the disadvantages of difficult selection of optimal conditions and insufficient yield [Org React ,, 21, 1 (19 9 4)]. Furthermore, SF 4 itself is toxic And corrosive, and there is danger of explosion during the reaction In addition, DAST can effectively fluorinate carboxyl groups and provide carboxylic acid fluorides, and can also be effectively used as the hydroxyl group, carbonyl group and other oxygen-containing fluorinating agents of the first, second and third alcohols. However, D AST has the problems of requiring special manufacturing equipment, being expensive, and having a high explosion hazard. The fluorinating agent of the present invention can eliminate these problems and can perform the fluorination reaction of carboxylic acids. The fluorine-containing compound thus prepared In recent years, it has received enthusiastic attention in the fields of life sciences such as medicine and agricultural chemicals, and it is also a raw material substance of functional materials. Carboxylic acid fluorination can be prepared using the fluorinating agent of the present invention as follows. In other words, the chemical formula of M (1 2) Compounds with fluorenic acid group R 15 -C00H (12)-37-(Please read the precautions on the back before filling in this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 530050 A7 B7 V. Description of the invention () R R is the same as M and reacts with the fluorinating agent of the present invention to prepare the acid represented by the chemical formula (1 2 -1) Fluoride: R 15 -COF (12-1) where is the same as on K. Representative carboxylic acids that can be used in the fluorination reaction include, for example, 9 formic acid, propionic acid, butyric acid, isobutyric acid, valeric acid, 3-methylbutyric acid, dimethylacetic acid, hexanoic acid, heptanoic acid, nonanoic acid, decanoic acid Acid Λlauric acid, myristic acid palmitic acid, stearic acid, phenylacetic acid, diphenylacetic acid, ethyl acetate phenylphenylpropionate cinnamic acid, oxalic acid, malonic acid, succinic acid, methylsuccinic acid , 1, 5-pentamethylene dicarboxylic acid, adipic acid Λ 1, 7-heptane dicarboxylic acid Λ suberic acid, azelaic acid, sebacic acid dodecanedioic acid, dodecanedioic acid and others Fatty bond tJCJ 単 carboxylic acid and diacetic acid cyclohexane carboxylic acid, p-methyl-1 -cyclohexanecarboxylic acid 2 -methyl-1 -cyclohexanecarboxylic acid, 3 -methyl-1-cyclohexanecarboxylic acid Acid 1, 3-Dicyclohexane — ▲ carboxylic acid Λ 1, 4-dicyclohexane fet dicarboxylic acid and other alicyclic hydrazones and dicarboxylic acids, benzoic acid% o-methylbenzyl acid, m-toluene Acid ·, p-Toluic acid 4-Isopropylbenzoic acid, 4-Zr-benzoic acid S m Methoxybenzoic acid Λ m-methoxybenzoic acid, p-methoxybenzoic acid \ methoxybenzoic acid Λ trimethoxybenzoic acid Λ-o-nitrobenzoic acid, meta-nitrobenzoic acid, p-nitrobenzoic acid, phthalic acid, isophthalic acid, Λ-phthalic acid and other aromatic monocarboxylic acids and monocarboxylic acids, and indole 2-hydrazone, indole- 3-Amino acid, Niacin and other heterocyclic carboxylic acids. However, there are no restrictions on these compounds. The acid fluoride compound represented by the chemical formula (1 2-1) can be prepared individually from the corresponding carboxylic acid. The amount of fluorinating agent to carboxyl group is usually 1 equivalent M. The reaction is usually carried out in a solvent. There are no special restrictions on solvents. This paper size applies the Chinese National Standard (CNS) Λ4 gauge (210 × 297). (Read the precautions on the back before filling in this page. R pack ·

Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs of the 1T. 530050 A7 B7 V. Description of the invention () As long as the dissolving surface does not react with the fluorinating agent used and the fluorinated acid fluoride produced. Preferred dissolving surfaces are acetonitrile, dichloromethane, dichloroethane, dimethylmethylamine, and 1,3-dimethyl-2-β mizolidinone. The reaction temperature depends on the reactivity of the solvent and the fluorenyl group, and is usually in the range of -40 to 100 ° C from the viewpoint of reaction rate and suppression of by-products, and M-20 to 80¾ is preferred. The carboxylic acid fluoride produced by the reaction can be easily separated from the reaction mixture via evaporation. (7) Fluorination via halogen exchange reaction The method of preparing a fluorine compound from a halogen compound other than a fluorine compound via a halogen exchange reaction using a metal fluoride is an orthodox method. Other fluorinated surfaces that have been used are tetrabutylammonium fluoride (TBAF), TBAF · HP, 701 HF-pyridine, and ginseng (dimethylamino-difluorotrimethylsilicate) (TASF). However, TBAF is hygroscopic and decomposes at high temperatures, so it must be handled with care. TASP has the problem of being expensive. The fluorinating agent of the present invention can efficiently synthesize fluorinated compounds through halogen exchange reactions. The fluorinating agent of the invention is used to exchange the halogen group of the compound with the fluorine group. Lipids or aromatic compounds having halogen groups other than the fluorine group can be used as the target compound for the fluorination reaction. However, when there is a When more than one electrophilic substituent (for example, nitro, carbonyl, cyano, trifluoromethyl or carboxyl group) is directly bonded to the aromatic ring, the halogen group directly bonded to the aromatic ring can more effectively utilize the present invention. A good example of the exchange reaction of fluorinated fluorinated hafnium is an aromatic compound having a halogen atom other than fluorine and represented by M chemical formula U 3):: This paper size applies Chinese National Standard (CNS) Λ4 gauge (210 × 297 公 #) _ 〇〇_ (Please read the back Note: Please fill in this page again. \ 装 530050 A7 B7 V. Description of the invention ((X i) d 乂 YOb (13) where X ^ is a halogen atom other than fluorine, d is an integer from 1 to 5, and Y 1 is an electrophilic substituent, b is an integer of 1 to 5, and b + d S 6 is a method (F) d for preparing a fluorine compound represented by the chemical formula (1 3 -1) by reacting with the fluorination reaction of the present invention d -(YOb (13 — 1) (Please read the precautions on the back before filling in this page.) Y 1, b and d are the same as the chemical formula (1 3). It has a halogen group which can be replaced by a fluorine group. Examples of the compounds include, for example, 2,4-dinitrochlorobenzene, 4-chloronitrobenzene, 2-chloronitrobenzene, 2,3,4,5,6-pentachloronitrobenzene, 3, 4, 5, 6-tetrachlorophthalic anhydride, 3, 4, 5, 6-tetrachlorophthalic acid with chlorine, 4, 4 *-dichloro-3, 3?-Dinitrobenzoic acid, 4 -Chlorotrifluoromethylbenzene, 4-chlorocyanobenzene, and 4-bromobenzaldehyde. However, halogen compounds are not limited to those on M. These halogen compounds individually provide correspondences represented by the chemical formula (1 3 -1) Fluorine compounds. Fluorination-the amount of halogen groups to be replaced by fluorine is 1 The amount is above, and M 1 to 10 equivalents are preferred. There is no particular limitation on the solvent, as long as the solvent does not react with the fluorinating agent, the compound having a halogen group, and the reaction product. The preferred solvent is acetonitrile. , Dichloromethane, chloroform, dichloroethane, 1,2-dimethoxyethane, diethylene glycol dimethyl ether, N-methylpyrrolidone, dimethylformamide, and 1,3- Two paper sizes are applicable to Chinese National Standard (CNS) Λ4 Regulations (210X297mmf)

Printed by 1T Shellfish Consumer Cooperative of Central Standards Bureau of the Ministry of Economic Affairs 4 0 530050 A7 5. Description of the invention The reaction temperature M is preferably in the range of 0 to 150 ° C, and more preferably 20 to 110 ° C. The fluorine compound produced by the reaction can be easily separated from the reaction mixture by distillation. The fluorinating agent can be recovered in K-related urea form after hydrolysis. (8) The fluorinating agent of the present invention can be suitably used for preparing a fluorine-containing olefin compound. In other words, the fluorine-containing olefin compound represented by M chemical formula (25):

Wherein R ίδ to R 1 7 are a hydrogen atom or a lower alkyl group having 1 to 3 carbon atoms * and may be the same or different; and Z is-(Y) n-CHF2, _ (Υ) n_CHF; or- CO-〇- (Y) n-CH2F, in which Y is -CH2- and η is an integer of 0 or 1 to 5, the preparation method includes the fluorinating agent represented by M chemical formula (1) and M chemical formula (2 4) Representation of hydrocarbon compounds

Printed by the Consumer Cooperative of the Central Bureau of Standards of Didi, where R to R 1 7 are hydrogen atoms or low-carbon alkane with 1 to 3 carbon atoms

And it may be the same or different; and X is -ί Y) n-CHO, -⑴η-C Η 2 OH, or-C 0-0-(Y) η-C Η 2 0 Η, where Y is- CH 2-an is 0 or an integer 0 to 1 to 5. The feminine used in the present invention is not particularly limited. The preferred hydrocarbon-returning compounds that can be used include fluorinated hydrocarbon species (chemical formula 26) with aldehyde groups at the molecular ends and _hydrocarbon species with hydroxyl groups at the molecular ends. This paper applies Chinese National Standards (CNS) Public #,), 1 530050 kl B7 V. Description of the invention (Chemical formula and olefin esters having a hydroxyl group at the molecular terminal (Chemical formula 2 8)) R1 5 R1 / (26) R 16 R15 R> c = c (/ R16 Υ ^ ΪΓ -C Η Ο (27)

γ is "-CH2〇H

R

R (Please read the notes on the back before filling this page) r

R Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Ethylene Dimethyl Ether (28) C7

II 〇 where R 15 to R 1 7 and Y are the same on M. These hydrocarbon-recording compounds are fluorinated -CHO group to -CHF2 group, and -CH20H group to -CH2F group, respectively, and respectively provide the corresponding formulas (26), (27,) and ( 28) a fluorine-containing olefin compound. In the fluorination reaction between fluorination_ represented by M chemical formula Π) and the homing compound having an awakening group represented by M chemical formula (2 6), the amount of bis-dialkylaminodifluoromethane to aldehyde fluorene is 1 equivalent M is preferred. When the fluorination reaction is performed on an olefin compound having a hydroxyl group represented by the chemical formula (27) or (28), the amount of bis-dialkylaminodifluoromethane to the hydroxyl group is preferably 1 equivalent. There is no particular limitation, as long as the solvent is inert 3 and does not react with bis-dialkylaminodifluoromethane and hydrocarbon compounds having a group or a hydroxyl group. The preferred solvents are acetonitrile, dichloromethane, chloroform, dichloroethane, ethylene glycol dimethyl ether, and N-methylpyrrolidine. This paper is in accordance with the Chinese National Standard (CNS) Λ4 Regulations (210 × 297) -4 2 530050 A7 B7 V. Description of the invention () Methylmethanamine and 1,3-dimethyl-2-azolidine noodles. The amount of the solvent is not particularly limited. However, from the standpoint of reaction efficiency and operability, its amount is preferably 1 to 10 times the weight of the substance. When the reaction is carried out, 5 alkali amines are added to the third amine to capture the generated hydrogen fluoride. The reaction temperature is not particularly limited. However, in the case of a feminine compound having an aldehyde group, from the standpoint of reaction speed and product stability, the thermometer is in the range of 0 to 150C, and W20 to 11 ° is preferred. In the case of a fluorene compound having a hydroxyl group, the humidity is in the range of -40 to 100 t, and M-20 to 80 ° C is preferred. When the hydrogen fluoride-based competitive reaction is removed, the reaction is preferably performed at a temperature as low as possible. The fluorine compound produced by the reaction can be easily removed from the reaction mixture by distillation. After the reaction is completed, the bis-diamidinodifluoromethane can be recovered as M tetraalkylurea. (9) The fluorinating agent of the present invention can be applied to the preparation of a fluorinated diamine diphenyl ring and a fluorinated diamine diphenylmethane which can be effectively used as a monomer of polyimide. In other words, it can be easily obtained in industry from 3,3 夂 dinitro (please read the precautions on the back before filling out this page) -Dichlorobiphenyl _ Preparation. The compounds described below.

This paper size applies the Chinese National Standard (CNS) A4 gauge (210 × 297 public) 4 3 530050 A7 V. Description of the invention () Using the fluorinating agent in the present invention can prepare the desired fluorine compound under appropriate conditions ° Section · W As shown in the above chemical formulas (a) to (f), 3,3'-dinitro-4, ^-dichlorodibenzo- (a) is used to prepare 4-chlorofluoro-3,3 ^ dinitro Dibenzoyl_ (b) ·, bis (3-nitro-4-chlorophenyl) difluoromethane (c), 3, 3, dinitro-4, 4 f-difluorobenzophenone ( d), 4-chloro-4 ^ fluoro-3,3, dinitrophenyldifluoromethane U), and bis (3-nitro-4-fluorophenyl) difluoromethane The increase in the molar ratio of 3 ^ dinitro-4, F-dichlorodiphenyl B can produce compounds having a larger number of substituted fluorine groups. In addition, by preparing compounds with a lower number of fluorinated fluorene and reacting the compounds with a fluorinating agent, compounds with a large number of fluorine groups can also be prepared for printing by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Discharge. For example, fluorine compounds (F) can be prepared by using 2 equivalents of a fluorinating agent on the starting compound (a). The reaction shows the direct conversion of oxygen in (4) on M to fluorine, and the fluorination reaction on M (7) using the exchange reaction of halogen substituted on the aromatic ring. The fluorinating agent of the present invention can be used Made easy. The solvent, reaction temperature and other parameters are based on the reaction conditions in (4) and (7) above. The reaction shown in (8) is one of the preferable specific examples using the halogenated compound of the present invention to compound a compound having a ketone or halogen group. This paper size applies the Chinese National Standard (CNS) A4 regulations (210 × 297 male f) 4 and printed by the Ministry of Standards Bureau's Consumer Cooperatives 530050 A7 B7 V. Description of the invention () The following will explain the ib school formula ί 1 5) Halogenated. The halogenated compound of the present invention is represented by the chemical formula (1 5): R1 R3 丨 N eight R2 / \ R 4 (15)

IX 4 x5- In the chemical formula (1 5), X 4 and) (5 are the same or different halogen atoms, but X 4 and X 5 are not fluorine, chlorine or bromine atoms at the same time. Combination of X * and X5 It is FC, F-Br, FI, C] -Br, C, I and II. In addition, when the halogen atoms of X 4 and X 5 are different, atoms with lower atomic weight are liable to form covalent europium, and have higher fluorene. Atomic weight atoms tend to form ion pairs. R5 to R4 are the same or different, substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted aryl. R 1 and R 2 or R 3 and R 4 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. ^ And R3 may be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. Preferred alkyl or aryl groups are preferred Has 1 to 6 carbon atoms. Alkyl is a straight or branched fluorene, which is methyl, ethyl, n-propyl, allyl, isopropyl, n-butyl, butenyl, n-hexyl or phenyl And they may be the same or different. In addition, R 1 and R 2 or R 3 and R 4 may be respectively bonded to form a heterocyclic ring having a nitrogen atom and 3 to 5 carbon atoms. Examples of such rings Pyrrolidine ring and hexahydropyrimidine ring. In addition, R 1 and R 3 may be combined to form a 5- or 6-membered heterocyclic ring including two nitrogen atoms, such as a pyrazidine ring, a pyridazolium ring, a pyrimidine ring, and Pyrimidine _ ring ΰ This paper size is applicable to Chinese National Standard (CNS) Λ4 gauge (210 × 297 public 牦) -4 5-(Read the precautions on the back before filling this page)

Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs 530050 A7 B7 V. Description of the Invention (M) Chemical formula U 5) The preferred practical examples of the halogenating agent include the following compounds. However, the scope of the present invention is not limited to these exemplified halogenating agents. Examples of chloride include: tetramethyl-2-fluoromethyl-iron = chloride, tetraethyl-2-fluoromethylsulfonium chloride, tetra-n-propyl-2-fluoromethyl-iron = chloride, tetraiso Propyl-2-fluoromethylsulfonium benzyl chloride = chloride, tetra-n-butyl-2-fluoromethylsulfonium iron = chloride, tetra-n-pentyl-2 -fluoromethylsulfonium methylbenzene == chloride, tetra-n-hexyl-2- Iron formamidine = chloride, 2-fluoro-1,3-dimethyloxazolidine = chloride, 2-fluoro-1, 3-diethyl-oxazolium ironsulfonium chloride, 2-fluoro- 1, 3 -di-n-propyl_oxazoline 钂 = chloride, 2-fluoro-1,3-di-n-butylhoetozolium iron = chloride, 2-fluoro-1, 3 _di-n-pentyl 眯 owa Ferroline = Chlorinium chloride, Fluoro-1,3-di-n-hexylhexazolidine = = chloride, Ν, Ν -dimethyl-fT, -methylphenyl monofluoromethane iron = chloride, and fluorine -Bis (1-hexahydropyridyl) methyl bond = chloride c Examples of bromide blue include: tetramethyl-2-fluoroformamidine_ = bromide, tetraethyl-2-fluoroformamidine_ = bromide Compounds, tetra-n-propyl-2-fluoromethyl bromide, tetra-isopropyl-2-fluoromethane iron = fluoride bromide, tetra-n-butyl-2-fluoromethane iron = bromide, this paper is applicable to China National Standard (CNS) Λ4 gauge Taiwan (210X29 7 公 #), p (please read the precautions on the back before filling this page) r Binding · Order A7 B7 V. Description of the invention () Tetra-n-pentyl-2-fluoromethylfluorene_ = bromide, tetra-n-hexyl- 2-fluoroformamidine iron = bromide, 2-fluoro-1,3-dimethylfluoride &gt; $ xoroline clock = bromide, 2-fluoro-1 s 3 -diethylhexyl chloride = desert 5 2 -fluoro-ί, 3 -di-n-propylfervalin iron = bromide, 2-fluoro-1,3-di-n-] yl_azole_iron = bromide, 2-fluoro-1,3 -di N-pentyloxazoline iron = bromide, 2-fluoro-1,3-di-n-hexylhexazolium «iron = bromide, N, N-dimethyl-N, -dimethylphenyl-fluoromethane Bell = bromide saddle f fluoro-bis (1-hexahydropyridyl) methyl iron = bromide, tetramethyl-2-chloromethanyl iron = bromide, tetraethyl ~ 2 * ~ chloroshenmai_ = Bromide * 2-chloro-1,3-diΦoxazolyl iron = bromide, and 2-chloro-1,3-diethyl-oxazonium iron = bromide. Examples of iodination include: Tetramethyl-Z-fluoromethyl lung surface = iodide, tetraethyl-2-fluoroformammonium iron = iodide, Tetra-n-propyl printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs- 2 -Fluoroformyl iron = gravel compound, tetraisopropyl-2 -fluoromethylpyridine iron = reading compound, tetra-n-butyl-2 _fluroformyl iron = iodide, tetra-n-pentyl-2 -fluoromethane _ = Iodide, Tetra-n-hexyl-2 -fluoromethylene ferrofluoride = Iodide, 2-Fluoro-1, 3 -dimethyl_azole, Iron = Compound, 2-Fluoro ~ 1, 3-diethyl_azole Scared iron = Echemical, 4 7 This paper size applies to Chinese National Standards (CNS) Λ4 gauge Taiwan (210X297 公 #) Printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs

530050 A7 B7 V. Description of the invention () 2-Fluoro-1,3-di-n-propyl azoxyzolium iron = iodide, 2-fluoro-1,3 -di-n-butyl_azole hydrazone = iodide, 2- Fluoride-1 5 3 -di-n-pentylimidazolium iron = iodide, 2-fluoro-1,3-di-n-hexyloxazoline clock = iodide, N, N-dimethyl-fluorene, Γ-dimethyl Phenylphenyl-fluoromethane iron = iodide, fluoro-bis (1-hexahydropyridyl) methyl iron = iodide_, tetramethyl-2-chloromethyl_bell = iodide * tetraethyl-2 -Chloroformamidine = iodide, 2-chloro-1,3-dimethyloxazole «iron = iodide, 2-chloro-I 3-diethyl_oxazoline iron = iodide, tetramethyl- 2 -iodoformamidine = iodide, tetraethyl-2-methosium iodide, 2-sulfo-1, 3-dimethyl_oxazonium I = iodide, 2 ~ zhen-], 3-di Ethyl_azole iron = iodide. Tetraalkyl-fluoromethyl P ί_ = halide is a preferred compound, and can react with alcohol under relatively mild conditions. K can be obtained by making the opposite ion (X 5) and the compound represented by the chemical formula (1 5) The halogen compound 0 prepared by the above alcohol hydroxyl exchange is particularly preferable: 2-fluoro-1,3-dimethyloxazole represented by the chemical formula (18) _face = chloride: H3 C—N N—C Η3 F Cl — This paper size applies Chinese National Standard (CNS) A4 gauge (210X29D &gt;#) (Read the precautions on the back before filling in this page

1T 530050 A7 B7 V. Methyl_oxazonium bell represented by the description of the invention (M chemical formula U 9) :: desert H3 C—N ι N—C Η (19) FB r K chemical formula (20) 2- Fluoro-1,3- &quot; Dimethyloxazole iodide H3 C—N +. N—C Η (20) (Read the precautions on the back before filling in this page

F Μ 2-Chloro-1,3-dimethyl_azole represented by chemical formula (21) = bromide

Hs C—N +. N—C Η (21) Order

CB r M 2-Chloro-1,3-dimethyloxazoline noodles represented by chemical formula (22) = town compounds: printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs Η 3 C —N +. Ν — C Η ( twenty two)

C 2 -Phosphorus_1,3-dimethylimidazole represented by chemical formula (23) = iodideΗ 3 C —N +. Ν — C Η (23) The paper size applies to Chinese National Standard (CNS) Α4 Specifications (210X 297 公 # 49 530050 A7 B7 V. Description of the invention () These halogenated surfaces can be applied to various halogenation reactions in the present invention. The desired halogen compounds can be used by the appropriate reaction agent according to the reaction on the M It can be obtained by carrying out a desired halogenation reaction. In this section, halogenated alcoholic hydroxyl groups using these Λ-forming agents can selectively provide a halogen compound of the opposite ion (X 5) in the chemical formula (1 5). In other words, make the chemical formula Π 1 Compound containing alcoholic hydroxyl group represented by): R 11 -0Η (8) where R u is a substituted or unsubstituted alkyl group, and which may contain an unsaturated group, and react with a halogenating agent represented by the chemical formula () 5) ; (Please read the notes on the back before filling in this page.

, 1T

X 4 χ 5 Among which X 4, X 5, and R 1 to R 4 are the same as those on M, and a fluorine compound represented by the chemical formula "8-1" is prepared: R11-X5 (8-2) Employees of the Central Standards Bureau of the Ministry of Economic Affairs Consumer cooperatives print which are substituted or unsubstituted alkyl groups, and which may contain unsaturated groups, and X 5 is a halogen atom. Examples of alcoholic hydroxy compounds that can be used in this reaction include methanol, ethanol, n-propanol, n-butanol, isobutanol, 2-methylbutanol, n-pentanol, neopentyl alcohol, isoamyl alcohol, n-hexane alcohol, 2-methylpentanol, 2-ethylbutanol, n-nonanol, 3, 5 5 5-trimethylhexanol, n-decanol, n-undecanol, n-dodecanol, allyl alcohol, methyl Allyl alcohol, crotonyl alcohol, benzyl alcohol, phenylethanol, cinnamon ferment, this paper size is applicable to the Chinese National Standard (CNS) A4 regulations (21 × 29h &gt; $) Γ Α Printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs 530050 A7 B7 5. Description of the invention () 2-propynol and other first alcohols; and isopropanol, second butanol, second pentanol, second isoamyl alcohol, 1-ethylpentanol, 1, 3 -Dimethylbutanol, 1-methylhexanol, 1-ethylpentanol, 1-ethylpropanol, 4-methyl-2-pentanol, 1-methylhexanol, 1-ethylpentanol Alcohol, 1-methylheptanol, cyclohexanol, 2-methylcyclohexanol, 3-methylcyclohexanol, 4-methylcyclohexanol, second phenylethanol and other second alcohols; and third Butanol, tertiary pentanol, 1-methylcyclohexanol, α-terpineol, and He third alcohol. However, the alcoholic hydroxy compound is not limited to these compounds. The amount of halogenated p-alcoholic hydroxyl groups is usually 1 equivalent M. There is no particular limitation on the solvent, as long as the solvent does not react with the reaction matrix, reaction reagent, and reaction product. The solvents are acetonitrile, dichloromethane, dichloroethane, ethylene glycol dimethyl ether, dimethyl ether dimethyl ether, dimethyl methylamine, 1,3-dimethyl-2-oxazole II, benzene , Toluene and hexane are preferred. The reaction temperature is usually -40 to 100 ° C, and preferably M-20 to 80 ° C. The resulting product can be easily separated from the reaction mixture via distillation. In addition, the reaction may be performed in the presence of a hydrogen halide capture surface, an alkali, and an acid catalyst, as long as these materials do not adversely affect the oxygen-containing functional compound of the halogenated surface represented by the chemical formula (15) and the reaction product. The halogen compound produced by the reaction can be easily separated from the reaction mixture via steaming. When the compound represented by M chemical formula U 5) remains unreacted, the generated hydrogen halide can be captured by adding hydrogen carbonate. In addition, after the completion of the reaction, the halogenated surface represented by the chemical formula (15) can be recovered in the form of urea in the related form. The carboxylic acid dentate represented by the chemical formula (12-2): R 15 -COXg Π2-2) The paper size is applicable to the Chinese National Standard (CNS) Λ4 gauge (210X 297 公 #) rn (Read the precautions on the back before reading (Fill in this page again.) Pack 530050 A7 B7 V. Description of the invention () where R 15 is substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted aryl, and X s is M The halogen atom represented by X 4 or X 5 in the chemical formula (1 5 &gt;) can be obtained by using a carboxylic acid compound represented by the chemical formula (1 2): R 15 -C00H (12) where R% is the same as the chemical formula (1 2- 2) It is the same as M, where the chemical formula (1 5) represents 0 produced by reacting the halogenating agent on the K printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs.-> The carboxylic acid halide group has an individual opposite to the chemical formula. X4 and χ5 halogen atoms in (15). When X4 on the halogenating agent of chemical formula (15) is F and X 5 is Br, carboxylic acid bromide, carboxylic acid fluoride, carboxylic acid anhydride, and fluoric acid fluoride are formed. fb has the highest Selectivity. When 'U is F and X 5 is I on the halogenating agent of chemical formula (15), carboxylic acid iodide, carboxylic acid fluoride, acetic anhydride, and fluorenic acid η 1C are more selective. The formation of carboxylic acid halides cannot be confirmed. Representative compounds with carboxyl groups that can be used for reluctance include, for example, formic acid, acetate, propionate, butyrate, isobutyric acid, valeric acid, 3-methylbutyric acid, formazan acetate, hexanoic acid, heptanoic acid, Λ-octanoic acid. Λ nonanoic acid, capric acid lauric myristic acid palmitic acid, fatty acid, phenylacetic acid, diphenylacetic acid, acetic acid \ phenylpropionic acid, cinnamic acid Λ oxalic acid, malonic acid, succinic acid Λ a Succinic acid 1, 5 -diacetic acid hexanoic acid, 1, heptane carboxylic acid Λ suberic acid Λ azelaic acid sebacic acid, dodecanoic acid, icosyl fatty acid and glutamate chain carboxylic acid and Dicarboxylic acid rms m hexylcarboxylic acid 1-methyl-1 -Cyclohexylcarboxylic acid, 〇_.methyl-1 -cyclohexylcarboxylic acid, 3-methyl-1 -cyclohexyl acid 1,3- • dicyclohexyldicarboxylic acid, 1, 4- • dicyclohexyl Acetic acid and other lipids Carboxylic paper This paper applies the Chinese National Standard (CNS) Λ4 gauge (210X297 公 #) 5 2 Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Distillation 530050 A7 B7 V. Description of the invention () Carboxylic acids; benzoic acid, benzoic acid, m-toluic acid, p-toluic acid, 4-isopropylbenzoic acid, 4-tert-butylbenzoic acid, o-methoxybenzoic acid, m-methoxybenzoic acid, p-methoxy Benzoic acid, dimethoxybenzoic acid, trimethoxybenzoic acid, o-nitrobenzoic acid, m-nitrobenzoic acid, p-nitrobenzoic acid, phthalic acid, isophthalic acid, terephthalic acid, and other aromatic monofluoric acids And dicarboxylic acids; metoin-2-junic acid, s? F sialo-3-junic acid, acids and other heterocyclic carboxylic acids. However, back-based compounds do not lie on these compounds. The amount of halogenated facing carboxyl group is usually 1 equivalent M. There are no special restrictions on solvents, as long as the solvent does not react with the reaction matrix, reagents, and production books. Preferred solvents are ethyl acetate, dichloromethane, dichloroethane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, dimethylformamide, 1, 3-dimethyl-2- _ Amidazine, benzene and toluene. The reaction temperature is usually -40 to 100 t, and preferably M-20 to 801. The resulting product can be easily separated from the reaction mixture via distillation. In addition, _hydrogen capture surface, alkali and acid catalyst can be added to the reaction system, as long as these materials will not adversely affect the halogenating agent, oxygen-containing functional compound and reaction product represented by the chemical formula (15) . The halogen compound formed by the reaction can be easily separated from the reaction mixture by distillation. When the compound represented by the chemical formula (15) remains unreacted, the generated hydrogen halide can be captured by adding sodium bicarbonate. In addition, after the reaction is completed, the fluorine compound represented by the halogenated _ Μ Μ chemical formula U. 0-2) can be recovered in the form of urea in the form of M: The paper standard is applicable to the Chinese National Standard (CNS) Λ4 regulations (210 '乂 297 public) -5 ό-(Please read the precautions on the back before filling this page)

530050 A7 137 V. Description of the invention () R-C Η X 7) 2 U0-2) where R 12 is substituted or unsubstituted, saturated or unsaturated alkyl, or substituted or unsubstituted aryl, And X 7 is a halogen atom represented by X 4 or X 5 in the chemical formula (1 5) of M, and the two X 7 are different, and can be compounded through an aldehyde represented by the chemical formula of M (1 0):: R 12 -CHO (10) where R 12 is the same as the chemical formula (1 0-2) and is prepared by reacting with a halogenating agent on K. When the halogenating agent X4 is F and X5 is C1 in the chemical formula (15) when methyl halide is halogenated, the methylformyl group is observed to be converted into chlorofluoromethyl and dichloromethyl. In this case, chlorofluoromethyl can be obtained with higher selectivity. Examples of compounds having a methylenyl group include, for example, Shenaldehyde, acetaldehyde, propionaldehyde, butyraldehyde, isobutyraldehyde, valeraldehyde, isovaleraldehyde, hexanal, heptyl, octaldehyde, nonanal, Decanal and other alicyclic aldehydes; benzaldehyde, p-nitrobenzaldehyde, p-methoxybenzaldehyde, phthalaldehyde, fluorenaldehyde and other aromatic aldehydes; cyclohexane aldehyde and other alicyclic aldehydes; and nicotine Aldehyde, pyranaldehyde and other heterocyclic rings_ Printed by the Consumer Standards Cooperative of the Central Bureau of Standards of the Ministry of Distillation, etc. This is a material-based combination of formaldehyde, which does not vary in the limit, and 0 Μ Solvents with no blending agents are available for the second test of alkane transethyl and chlorine agents, alkane transmethyl, chlorinated diyl, nitrile transethyl, and the solvent of solvent is better than that of C- only. In contrast, the special product amine methyl methyl ether ether glycol diethylene glycol_diethylene glycol diethyl benzyl and benzene pyrimidine peak I 2 i is based on ο P ο 0 ri 1—i. V 2 is mixed with Μ, should be t; reaction ο 5 is easy to be normal, and the distillation temperature is determined by the reaction 5 4 This paper size applies Chinese National Standard (CNS) Λ4 regulation (210X2Q7 public expense) 530050 A7 V. Description of the invention () In addition, the reaction can be carried out in the presence of _ hydrogen capture agent, alkali and acid catalysis_, so long as this The isocyanate will not adversely affect the halogenation of the chemical formula (15), the oxygen-containing functional compounds, and the reaction. The halogenated compound formed by the reaction can be easily separated from the reaction compound by distillation. When the halogenating agent represented by Chemical Formula (15) remains unreacted, the generated hydrogen halide can be captured by adding hydrogen carbonate M. In addition, after completion of the reaction, the halogenated surface represented by the chemical formula (M) (5) can be recovered in the urea form of phase M. The halogenation of these M chemical formulas (1 5) to (1 7) can be achieved by making the compound represented by M chemical formula (1 4): (Please read the precautions on the back before filling in this page. . Ν Eight R2, with

R (14), -port

IX 2 X where X 2 and X 3 are chlorine or bromine atoms; R 1 to R 4 are substituted or not printed, substituted or saturated alkyl, or substituted or Unsubstituted aryl, and they may be the same or different; R 1 and R 2 or R 3 and R 4 may be conjugated to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms; or 1 to 3 may be bonded In order to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms, it is expected that an alkali metal salt of a halogen can be safely and easily prepared by performing a halogen exchange reaction in an inert solvent. The compound represented by M chemical formula U 5) can be used as it is as a chlorinating agent or brominated surface. However, in order to obtain halogenated noodles with high reactivity, alkali metal salts with fluorine such as fluoride planers, fluoride enzymes, potassium fluoride or sodium fluoride are used. 5 This paper is in accordance with Chinese National Standard (CNS) Λ4 regulations.台 （210Χ 297 公 #） 530050 ΕΠ 5. Description of the invention () reaction, and the production of myelin tetraalkyl-2_fluoromethyl clock = chloride, once it can be used as a chloride or brominating agent ϋ Compounds having a chlorine atom at positions X 2 and X 3 can be used to prepare bromide, and sodium bromide, potassium bromide, and other alkali metal salts of bromine can be used. When an iodinating agent is required, dysprosium, iodide, potassium iodide, and sodium iodide can be used. The halogenating agent represented by M chemical formula U 5) is prepared from the compound M represented by M chemical formula (1 4 &gt;) as previously described. In preparing the halogenating agent represented by M chemical formula (1 5) in the present invention, The amount of the alkali metal salt of the halogen in the halogen exchange reaction to the compound represented by the chemical formula (14) is preferably 2 equivalents M, and more preferably 2 to 5 equivalents. When the amount is less than 2 equivalents, it is not satisfactory. On the other hand, the amount of more than 5 equivalents does not sufficiently improve the yield. There is no particular limitation on the solvent used in the element exchange reaction, as long as the solvent blue does not react with the chemical formula U 4) The indicated compound and the reaction product may react. Preferred solvents are acetonitrile, dimethylformamide, 1,3-dimethyl-2-oxazolyl, dichloromethane and dichloroethane. There is no special restriction on the amount of solvent printed by the Shell Standard Consumer Cooperative of the Central Bureau of Standards of the Ministry of Economic Affairs. However, from the standpoint of reaction efficiency and workability, the preferred amount is 1 to 10 times the weight of the reaction substrate. From the viewpoint of the reaction rate and the stability of the compound to be formed, the reaction temperature is usually in the range of -20 to 150, and M 0 to 100 ° C is preferred. The iodinating agent is prepared in the range of 0 to 80 C in nitrogen under the light-shielding, and it is better to suppress the oxidation of the iodinating agent. The halogen exchange reaction on M can also be used in phase transfer catalysts such as the fourth alkyl paper standard applicable to the Chinese National Standard (CNS) Λ4 gauge (210X29D &gt; i) _ „530050 kl B7 5. Description of the invention () Ammonium salt and the fourth The alkyl scale salt is coexisted. The reaction mixture containing the generated halogenating agent represented by the chemical formula (1 5) of K can be used as it is for the next halogenation reaction, or the inorganic salt can be filtered and the solvent can be distilled off. It is used in the next halogenation reaction. The halogenating agent represented by the chemical formula (15) above M can also be carried out in an inert solvent by using a fluorinating agent represented by the chemical formula (1) of the present invention and a base of chlorine, bromine or iodine atom. The metal salt is prepared by the element exchange reaction. The reaction can be carried out using almost the same reaction conditions as the above-mentioned halogen exchange reaction. The present invention will be further described in detail through examples below. However, these examples are not limited The scope of the invention. In Example 1, after conversion to a derivative by reaction with aniline, 2,2-difluoro-1 was measured by high performance liquid chromatography (hereinafter referred to as HPLC method). The concentration of 3 -dimethyl-oxazodine (hereinafter referred to as DPI) in ethyl acetate solution. The concentration of fluoride ion (hereinafter referred to as F-) is determined by absorption using alizarin ion reagent. Example 1 2 The synthesis of 2,2-difluoro-1 5 3 -dimethyl_azolidine (DFI) was printed in a 500-ml four-necked reaction bottle with 76 * 4 grams (0.452 Mo Ear) of 2-Chloro-1,3-Dimethyl thiazolidine iron = chloride, 105,2 g (1.8 10 mol) of spray-dried potassium fluoride, and 320 ml of acetonitrile, and under nitrogen The reaction was carried out at 80 ° C for 17 hours. After the reaction mixture was cooled to 25 ° C, the inorganic salt was separated from the reaction mixture to obtain a solution of 41.2 g of DFI (MW 136 * 15) in acetonitrile. DFI in the solution The concentration is 11 * 4 weight percent. The yield is 771. The reaction mixture is vacuum distilled to obtain 32 g of DFI with a purity of 97.8. I This paper size applies to Chinese national standards (CNs &quot; rA4 specifications (210X 297 公 #) -5 / 530050 A7 B7 V. Description of the invention () DFI has properties under M. Boiling point 47 · 0C / 37 mmHg, E IMS: 136 (Μ +), 1 17 (Μ +-"), IR (g &gt; cni name: 1486, 1385, 1 295, 1242, 1085, 966, 711, F-analysis; calculated value 27, 9¾, found 27, 7¾, 1 1-NMR (δ, ppm &gt; CDC13, TMSS): 2, 5 2 (s, 6 Η, -CH 3 x 2) &gt; 3,05 (s, 4H, -CH2CH2 '), 13 C Η MR δ δ, ρριπ , CDC13, -45 ^ CDC I 3 group) m (s factory CH3x 2), 47,6 (s, -CH2CH2-), 128 * 5 (t, J = 2 30 Hz, = CF2), 19 F NMR ( δ, ρρπι, Ci) Cl3, -45 tj CFC 1 3 group): -7 (K9 (s, = CF2) cIR spectrum is shown in FIG. 1. Example 2 Synthesis of bis-dimethylamino-difluoromethane (hereinafter referred to as TMF) in 33.32 g (0.224 moles) of tetramethyl-chloromethylpneumonium = chloride dissolved in 107, 8 2 g 52.0 g (0.896 mol) of spray-dried potassium fluoride and 33 # 66 g of acetonitrile were added to the acetonitrile solution, and reacted at 85 ° C for 52 hours. The reaction mass was then filtered to obtain a TMF solution in acetonitrile. The properties of TMF were measured using ethyl acetate solution. Its properties are as follows. EIMS: 138 (M +), 119ίM-F) +, F-analysis: Calculated value 12,4¾ Printed by the Consumer Cooperative of the Central Standards Bureau of Didi Ministry, measured value 1 2, 1%, 1 Η-NMR δ ρ ρ in, C Η 3 C Ν solvent, C Η 3 C Ν group, 24 υ): 2,44 (s, -CH3), i3C NMR (5, ρρπ, CH3CN soluble surface, 24 ^ DMS〇-dBS): 3 6, 1 (s,-C Η 3 x 4) ^ 1 2 8. 6 (t, = CF 2) 〇 Example 3 Bis-di-n-butylamino-difluoromethane (hereinafter abbreviated as TBF) was synthesized in 74.36 g (0,2129 mol) tetra-n-butyl-chloroformyl chloride = 50.92 g (0.8864 mol) of chloride dissolved in 181.45 g of acetone solution. The size of this paper is sprayed to Chinese National Standard (CNS ) Λ4 specification (210X 297 public #) -58-530050 A7 B7 V. Description of the invention () Fog-dried potassium fluoride and 7.6 g of acetonitrile, and reacted at 85 ° C for 3 5 hours. The response will be filtered afterwards. The solution was separated into two layers. The two layers were mixed and distilled under reduced pressure. The resulting residue was TBF. The residue has properties under M. EIMS: 306 (Μ + 287 (MF) +, F- analysis: calculated value 12. «, found value 12,1«, 1 Η-ΝΜΚίδ, ppm, without solvent dilution, CH 3 CN group, 2 4; 1 ♦ 0 4 (tj = ~ 8 H z, CH 2 £), 1 ♦ 4 1 (nu j two ~ 8 Η z, CH 2 CJg C Η 3), L 5 9 (quintet, j = ~ 8 Η Z, CH2CH2CH2) ^ 2,92 (1, j = ~ · 8Ηζ, Ν £ Η2〇Η2) ^ iS CNMR (δ 5 pp in, without solvent dilution, 2 4 ° C, DMS 0 _ d 6 group): 1 2. 8 (CH 2 CJi ^)-1 9. 6 (CH 2.Cli 2 CH 3) ^ 3 0 + 2 (CH 2 CJ 2 CH 2) ^ 46.3 (NCH2CH2), 128.2 (t, j = 2 48 Hz, CF2)-Example 4 Printed 2,2-difluoro-1,3-di-n-butyl-oxazole (M hereinafter referred to as DFB) synthesized by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs in a reaction vessel Filled with 5 1 ♦ 7 g (〇, 1 84 mol) purity 9 0 I 2 -chloro-1, 3-di-n-butyl_oxazoline surface = chlorinated, 174 g of acetonitrile and 6 4.3 g (1.11 mol) of spray-dried potassium fluoride and reacted at 8 5 ° C for 25 hours under a slightly increased nitrogen pressure. After cooling, the reaction mass was passed to obtain an acetonitrile solution of DFB. .Make Solution measurement properties. 1 H-HMR (δ, ppm ^ CDCi: 3, TMS group, 2 5 Τ;}: 0,93 U, j --8Hz, CH2CH3)-1. 40 (10, j = ~ 8Hz, CH2CH2CH3)-1,56 (five clocks, j = ~ 8Hz, CH2〇 ^ CH3), 2.95U, ~ 8Hz 'NCJl2_CH2)-3.24 (s, NCH2CliiN) ^ 13 C NMR (δ, ppio, CDC 1 3, -6 5 υ, CDC i 3 basis &quot; 1 3, 4 (s, CH 2 〇3), 1 9 ♦ 4 (s, this paper size applies Chinese National Standard (CNS) A4 specification (210X 297 male f)- 5 9-530050 Μ B7 V. Description of the Invention (CH2 £] 1_ £ CH3), 2 £ K 1 (SiCH2 £ J £ CH2), 45, 1 (s, NLH £ CHzCH2), 4 5.5 (s, HCH 2 CH 2 N) ^ 1 2 8, 9 (t, j = 2 2 8 H z »CF 2) 〇 Example 5 Synthesis of benzyl-fluoride in a reaction vessel was charged with 2 3. 8 9 g (0 0.2 Molar) DFI prepared by a procedure similar to that in Example 1 was dissolved in a 11.4 weight percent solution of acetonitrile, 2.44 g (0.02 mole) of benzoic acid and 8 ml of acetonitrile, and under nitrogen at 25 υ The reaction took 4 hours. After the reaction was completed, a part of the reaction mixture was taken out and subjected to GC-MS measurement. The results confirmed the formation of benzamidine fluoride (the main ion, 124). The reaction yield measured by GC analysis was 981. Comparative Example _ Example 1 Synthesis of benzamidine fluoride Charge 0.79 g (3.0 moles) into a reaction vessel. 2-Fluoro-1,3-dimethyl_azole prepared according to the preparation method described in W096 / 04297. Printed by the Consumer Standards Cooperative of the Central Standards Bureau of Didi Ministry = Hexafluorophosphate, 0.2 g (2.0 mmol) benzoic acid and 15 ml acetonitrile, and under nitrogen at 25 ° C The reaction took 4 hours. After the reaction was completed, the reaction mixture was analyzed by GC. Results M77I yielded benzyl_fluoromonomer. Example 6 Synthesis of benzyl fluoride was charged in a reaction vessel (1.783 g Π.50 mmol). DFI prepared by the procedure of Example M in Example 1 was dissolved in acetonitrile. Η. 4 weight percent solution, (K162 g (1.50 mmol) benzyl alcohol and 6 ml of acetol, and react under nitrogen at 25 3C for 4 hours. After the reaction is completed, the reaction mixture is subjected to this paper scale applicable to China National Standard (CNS) Λ4 gauge (210X 297 ^ ¥) -b ΰ-530050 A7 V. Description of the invention () GC-MS measurement. The results confirmed the formation of benzyl fluoride (main ion, 110). Measured by GC analysis The reaction yield was 831. Comparative Example 2 Synthesis of benzyl fluoride 0.40 g (15 mmol) was placed in a reaction vessel according to the preparation method described in W096 / 0 4 2 9 7 2-Fluoro- 1,3-Dimethyl_azole scare = hexafluoropic acid salt, 0.162 g (1.5 mmol) of benzyl alcohol and 6 ml of acetonitrile, and reacted under nitrogen at 251 C for 4 hours. GC analysis of the mixture. No stupid methyl fluoride was detected. Example_7 The synthesis of fluoro-n-octane was approved by the Central Standards Bureau. Printed by the Industrial and Commercial Cooperatives in the reaction container containing 1.79 grams of U.50 millimoles) (114% by weight of DFI dissolved in acetonitrile prepared in the same procedure as in Example 1 and 0.195 grams of U.50 millimoles) N-octanol and 4 ml of acetonitrile, and reacted under nitrogen at 2510 for 4 hours. After the reaction is completed, G C ~ MS measurement is performed on the reaction mixture. The si produced fluoro-n-octane fei (mainly apart from 10, 1 2 2) 荦 production of 荦 was 801 〇 Example 8 Synthesis of fluoro-n-octane was charged into a reaction vessel 4.15 g (5.29 mmol) in the example 2 The prepared TMF was dissolved in 17.56 weight percent of ethyl acetate, 0.275 g (2.55 mmol) of n-octanol and ethyl acetate, and reacted under nitrogen at 25 t) for 4 hours. After completion of the reaction, the formation of fluoro-n-octane (main ion, 132) was confirmed by GOMS measurement of the reaction mixture. Analysis by GC_Reaction yield obtained by this paper This paper is in accordance with Chinese National Standards (CNS) Λ4 gauge (210X297 male f „1 530050 A7 B7 V. Description of the invention () Printed by the Consumers Cooperative of the Central Bureau of Standards of the Ministry of Printing as 9 6 I & Example 9 Fluoroxocin was filled in a reverse me container and filled with 0 ♦ 9 grams (2, 9 millimoles) of Fang Lingshi_ Example 3 A TBF having a purity of 91% was prepared. 0, 15 grams (1''5 millimolar) n-octanol and 6 ml of nitrile and flying at 25 t under nitrogen; reaction for 4 hours; after the reaction is completed 5 confirmed by the GC-MS tide volume of the reaction mixture to produce fluorinated Syringe (main ion 132) 0 The reaction yield measured by GC analysis was 9 8. 21-Example 10 The formation of fluoro-n-octane in an anti-m container was charged with 1 + 6 1 g (0, 77 mmol) Ear) DFB prepared in Example 4 with a dullness of 131, 0, 12 g (0 * 77 mmol) of n-octanol and 2 ml of acetonitrile f and reacted in m gas at 25 U for 1 hour. Yu Fan 5 After completion, GC-MS measurement of the reverse-mixed compound was used to confirm the formation of fluorinated symplenium (the main ion, 1, 32 ΐ &gt; the reverse yield was 90% measured by GC analysis. 3 Synthesis of fluoro-n-octane In a reaction vessel, 0,40 g (5 mmol) was charged. 2-Fluoro-1, 3-prepared according to the preparation method described in y0 96/0 42 9 7 Dimethyl oxazole iron = -Ju * / \ Pyrophosphate, 0, 195 g (1.5 mmol) n-octanol and 6 ml acetonitrile f and react in nitrogen at 25 '1C for 4 hours c &gt; Subsequent GC analysis of the reaction mixture ° Fluoro-octane was not detected. Example 11 Synthesis of Fluoro-Terpentane This paper is scaled to the CNS Standard (Cholera) 530050 A7 B7 V. Description of the invention () A reaction vessel was charged with 7.74 g (6.48 mmol) of DFI prepared in the same manner as in Example 1 in a 11.4 weight percent solution of acetonitrile, and 0.285 g (3, 24 millimoles Alcohol, and reacted under nitrogen at 25 ° C for 1 hour. After the reaction was completed, it was confirmed that the third tripentane (main ion, 90) was formed by GC-MS measurement of the reaction mixture. The reaction yield was 621. Example 1 Synthesis of 2,3-difluorobutane. A reaction vessel was charged with 7.74 g (6.48 mmol) of DFI prepared in the same procedure as in Example 1 and dissolved in acetonitrile. 11.4% by weight and 0,29 grams (3 * 24 mmol) of 1,3-butanediol, and reacted under nitrogen at 25v for 1 hour. After the reaction was completed, GC-MS measurement of the reaction mixture was confirmed to produce 1,3-difluorobutane (main ion, 93). The reaction yield was 61 «. Example 1 3 Difluorodiphenylmethane Synthetic Printing of Employees' Cooperatives of the Central Standards Bureau of the Ministry of Economics ^ Fill a reaction vessel with 2.43g (17.8mmol) of DFI prepared by the same steps as in Example 1, 1 + 63 grams (8.9 millimoles) of dibenzoyl ring and 20 milliliters of ethyl acetate, and reacted under nitrogen at 84t for 28 hours. After the reaction was completed, GC-MS measurement of the reaction mixture confirmed the formation of difluorodiphenylmethane (main ion, 204, base peak 127). The reaction yield measured by GC analysis was 451. Example 14 Synthesis of 1,1-difluorohexane and 1-fluoro-bucyclohexene This paper is sized to the Chinese National Standard (CNS) Λ4 specification (210 × 297).一 D ό 530050 kl B7 V. Description of the invention () Put i. 99g (1 I 7 millimolar) into the reaction container, DIM, CK85g (8,6) prepared by the same steps as in Example 1 Mol) cyclohexyl, δ, 5 g of 1,2-dimethoxyethane and 0 + 15 g of 25¾ oleum, and reacted under nitrogen at 20 to 251 C for 96 hours. After the reaction was completed, GC-MS measurement of the reaction mixture confirmed that 1,1-difluorohexane (main ion, 120) and 1-fluoro-cyclopentadiene (main ion, 100) were formed. The yield of fluoro-1-cyclohexene in the reaction obtained by GC analysis was 771. Example 1 Synthesis of 4,5,4,4-dichlorodifluorodiphenylmethane A reaction vessel was charged with 12.2 g (10.2 mmol of DFI) and a 0 "1 ethyl ester was prepared through the same procedure as in Example 1. Food solution, and 1 + 26 g (5.04 mmol) of 4,4 夂 dichlorodibenzoyl and reacted at 84 υ for 24 hours. After the reaction was completed, the formation was confirmed by GC-MS measurement of the anti-hall mixture 4,4 'dichlorodifluorodiphenylmethane (main ion, 272). The yield of 4,4'-dichlorodifluorodiphenylmethane in the reaction measured by GC analysis was 901. Implementation of 16 α, a -Difluorotoluene is produced by the Consumer Cooperative of the Central Standards Bureau, Ministry of Economic Affairs, printed in a reaction vessel, and charged with 12.43 g (17.8 mmol) of DFI prepared by the same steps as in Example 1, ( KK 93 g (8.8 mmol) of benzaldehyde and 25 ml of acetonitrile, and reacted for 8 poems under nitrogen at 80 υ. After the reaction was completed, it was confirmed by GC-MS measurement of the reaction mixture that α, σ -di was formed Fluorotoluene (main ion, 128). The reaction yield measured by GC analysis was 80P. Example 17 Synthesis of 4, 4 'difluorodibenzyl surface Applicable to Chinese National Standards (CNS) Λ4 standard orange (210 × 297) 一 6 4-530050 Μ B7 V. Description of the invention () Put 4,08 g (3 (K00 mmol)) into the reaction container Example 1 DFI prepared in the same procedure, 107 g (5,00 mmol) of 4,4 ^ dihydroxydibenzyl and 50 ml of ethyl acetate, and reacted under nitrogen at 84 ° C for 2 hours. After completion of the reaction, GC-MS measurement of the reaction mixture was performed to confirm that 4,4'-difluorodibenzo- (main ion, 218, base peak) 23 was formed. The reaction yield measured by GC analysis was 201 Example 18 Synthesis of methyl allyl fluoride A reaction vessel was charged with 1,783 g (1.50 mmol) of DFI prepared in the same manner as in Example 4 in a 4 weight percent solution of acetonitrile, (K 108 g (1.5 mmol) of methallyl alcohol and 6 ml of acetonitrile were reacted under nitrogen at 25 ° C for 4 hours. After completion of the reaction, GC-MS was performed on the reaction mixture. Measurement confirmed the formation of methyl feprofluoride (main ion, 74). The reaction yield measured by GC analysis was 951. Example 1 9 Synthesis of fluorocyclohexane Printed by the Central Bureau of Standardization, Shellfish Consumer Cooperative, put 1.783 grams (L50 millimoles) in a reaction vessel, and the DFI solution prepared in the same procedure as in Example 1 was dissolved in a 4 weight percent solution of acetonitrile, (K150 grams (1.50 milliliters) Mol) cyclohexanol and 6 ml of acetone, and reacted under nitrogen at 25 t for 4 hours. After the reaction was completed, GC-MS measurement of the reaction mixture was performed to confirm the formation of fluorocyclohexane (the main ion , 10 2) and cyclohexene (main ion, 82). The reaction yields measured by fflGC analysis were fluorocyclohexane 101 and cyclohexene 901, respectively. Example 20 This paper size applies the Chinese National Standard (CNS) Λ4 gauge (21〇 × 297297β) 65-Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Lithology 530050 5. Description of the invention () Synthesis of fluoroisopropane The reaction vessel was charged with 1.783 g (1.50 mmol) of DFI prepared in the same manner as in Example 1 in a 114 wt.% Solution of ethyl acetate, 0.09 g (L50 mmol) of isopropanol, and 6 ml of acetonitrile. , And reacted in nitrogen at 2 5 C for 4 hours. After the reaction was completed, it was confirmed that fluoroisopropane (the main ion, 62) and propylene (the main ion, 42) were formed by the amount of 0 (: -148) of the reaction mixture. ). The reaction yields measured by GC analysis were fluoroisopropane 801 and propane-201. Example 2 1 Synthesis of p-fluoronitrobenzene A reaction vessel was charged with 41.6 g (40.8 mmol) 13 * 6 DFI in acetonitrile, 2,84 g (20,4 mmol) of p-nitrophenol and 2,03 g (20 + 1 mmol) of triethylamine in nitrogen at 8 4 The reaction was carried out for 15 hours. After completion of the reaction, the formation of p-fluorine was confirmed by GC-MS measurement of the reaction mixture. Nitrobenzene (main ion, 141). The yield of the reaction by GC analysis was 601. Example 22 Synthesis of p-fluoronitrobenzene A reaction vessel was charged with 20 g (16.0 mmol) of 10.7 weight percent. A solution of DFI in acetonitrile, 1256 g (8.10 mmol) of p-nitrothiophenol, and reacted under nitrogen at 84 for 16 hours. After the reaction was completed, the reaction mass was poured into 20 ml of a saturated aqueous sodium hydrogen carbonate solution. The DFI was hydrolyzed in the medium, and the concentrated HC1 was continuously acidified to pH 2M and extracted with 50 ml of dichloromethane. The GC-MS measurement of the reaction mixture confirmed that p-fluoronitrobenzene was produced (the main ion is the size of the paper applicable to China) Standard (CNS) Λ4 gauge (210X 297 公 #) _ ίλ α _-^ yiyi-(** Please read 1 *. Note on the back before filling this page)

, 1T

C 530050 A7 B7 V. Description of the invention (), 141). The reaction yield measured by GC analysis was 201. Example 2 Synthesis of 3,2,4-Dinitrofluorobenzene In a reaction container containing 64 g of human L (8. 10 mmol) 2,4-m-chlorochlorobenzene and 2.21 g of U 6 * 2 3 millimolar) DF I, &gt; and 25 ml of acetonitrile, and reacted under nitrogen at 84 ° C for 7 hours. After the reaction was completed, GC-MS measurement of the reaction mixture confirmed that 2,4-nitropyridine fluorobenzene was generated (the main ion 5 18 6 f radical 9 4). The yield of anti-trfp measured by GC analysis was 9 6.01. Example 24 Synthesis of dichlorofluoronitrobenzene In a calendar container, 0 * 74 g (2.550 mmol) pentachlorom Benzene, 1,77 g (13,00 mmol) of DF I, and 25 ml of acetonitrile, and reacted under nitrogen at 84 Torr for 2 hours. After the reaction was completed, GC-MS measurement of the reaction mixture was performed to confirm the formation of dichlorofluoronitrobenzene (the main ion 9 245, the main ion + 2 247, the main ion + 4 249), the base peak 2 4 5 and the The yield measured by GC analysis was 28, 0. 1. It was also confirmed that trichlorofluoronitrobenzene (main ion 26 1, main ion + 2 263, main ion + 4 26 5, base peak 2 0 5) 5 and The yield was 1 1 ♦ 3%;-, and it was confirmed that tetrachlorofluorom-based benzene (main ion 2 7 7 5 main ion + 2: 2: 7 9 ί 5 main ion + 4 2 8 1 3 &gt; main ion + • 6 28 3 ^ • Base peak 22: 1) 9 and yield of 9, 0 «solid m Example 25 The synthesis of stupid saflufloxacin was printed by the Ministry of Standards and Staff's Consumer Cooperatives in the Ministry of Standards and loaded into the reaction container and filled with L41 G U0.03 mmol) benzoxachlor, 163 g (11,97 mmol) DFI, and 25 ml of acetonitrile, and under the nitrogen, the Chinese National Standard (CNS) Λ4 Regulations (210X) 297 records) ~ b / ~ 530050 A7 B7 V. Description of the invention () Reaction at 841 for 2 hours. After the reaction was completed, GC-MS measurement of the reaction mixture was performed to confirm the formation of benzyl fluoride (main ion, i24, base peak 124). The reaction yield measured by GC analysis was 71.1. Example 26 Synthesis of 2-Fluoro-1,3-dimethyl-Wafer_chloride (DMFC) A 200 ml four-necked reaction flask was charged with 30.42 g (0,1799 mol) of 2- Chloro-1,3-dimethyl-chlorobenzene = Chloride (DMC>, 1 5 * 1 1 g ((K 3 5 98 mol) of sodium fluoride and 104. 9 g of acetonitrile, and 8 small poems were reacted in nitrogen at 8 5 1 C. After the reaction mixture was cooled to 25, the inorganic salt was separated from the reaction mixture to obtain a solution of 116 + 09 grams of 08? (: "^ / 152,60) in acetonitrile. The concentration of DMFC in the solution is 2L01 weight percent, and the yield is 89¾. The physical properties are as follows: FABMS; 117 [(M-CI) +], 2 6 9 [(2 x MC 1) +], F — analysis: calculated value 2 * 6 w 11, measured value 2. 7 V? T%. C 1-analysis: calculated value 4 * 8 w 11; printed by t of the Consumers' Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs, measured value 4,9wtl〇1 Η-NMR (δ, ppir &gt; CH3CN solvent, CH3CN group, 2 5t;): 2, 98 (s, 6H, -CH 3 x 2) &gt; 3, 9 1 (s, 4 H,-CH 2 CH 2-) .13 C-NHR (5, ppm, CH3CN soluble surface, DMSO-cU group ^ 25tM: 31 * 3U, -CH3x 2) ·, 46,8 (s, -C H2CH2-), 1 5 7. 7 (d, J = 2 8 0 H z, CF) Example 27 Synthesis of chloro-n-octane is packed in a reaction vessel with human (K5789g (4 + 445 millimolar) Octanol, and 3.29 grams of 21,01 weight percent DMFC in acetonitrile (0,691 grams, this paper size applies the Chinese National Standard (CNS) Λ4 specification (210X 297 public #) 88 530050 A7 V. Description of the invention () 4,530 Dmol) and reacted under nitrogen at room temperature for 5 hours. After completion of the reaction, GC analysis of the reaction mixture showed that the yield of chloro-n-octane was 93.1 «. Unreacted n-octanol was 6.6 ¾. Comparative Example _ Example 4 The synthesis of chloro-n-octane was charged in a reaction vessel (K7333 g (5 + 631 mmol) n-octanol, and 0.956 g (5.6 5 5 mmol) DMC and 3 8 g of acetonitrile, and reacted under nitrogen at room temperature for 6 hours. After the reaction was completed, GC analysis of the reaction mixture showed that the yield of chloro-octane was 29.315. The unreacted n-octanol was 70.01. Example 28 Synthesis of n-Benzamidine Chloride A reaction vessel was charged with (K566 grams (4 * 636 millimoles) benzoic acid and 3 + 34 grams of 21.01 weight percent 08? (: Acetonitrile solution (0,707 grams, 4,636 Dmol) and reacted under nitrogen at room temperature for 3 hours. After the reaction was completed, GC analysis of the reaction mixture showed that the yield of benzyl chloride was 9 1 ♦ 91 and the yield of benzyl fluoride The rate is 8,01. Example 2 9 The synthesis of σ-chloro-α-fluorotoluene printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Economic Affairs was charged in a reaction vessel (K9935 g (9.361 mmol) benzaldehyde and 6 * 81 g of 2 1.01 weight percent DMFC in acetonitrile (1.431 g, 9.4 mmol of DMFC &gt;) and reacted at 85 ° C for 17 hours under nitrogen. After the reaction was completed, the reaction mixture was GC-MS Measurements confirmed the formation of 0 (-chloro-ot-fluorotoluene (main ion 144, base peak 109) and benzyl chloride (main ion 160, base peak 125). Α-Chloro-α-Fluorine measured by GC analysis The yield of toluene is 63. 61. The paper size is applicable to the Chinese National Standard (CNS) Λ4 gauge (210X29? ^ #) -D 9 ~ 530050 A7 B7 5 2. Description of the invention () The yield of benzyl chloride printed by the Consumer Cooperative of the Central Standards Bureau of the Ministry of Lithium is 19.71 and the unreacted benzaldehyde is 1 4,51 0 negative example 3 0 / — fluorine-1, 3- Synthesis of bis 1 methyl_oxazoline bromide (DMFB) A 300 ml four-necked flask was charged with 1 3,78 g (0 + 1 0 1 mole) of 2, 2-difluoro-1 ' 3-Dimethyltriazolidine (DFI), 10 * 25 g (0.095 5 mol) of sodium bromide, and 126, 5 g of acetonitrile, and under nitrogen at 25 ° C The reaction was carried out for 4 hours. The yield of 2-fluoro-1,3-dimethyl-Wamen = bromide was 991. The physical properties are as follows. FABMS; 117 [(M-Br) +], 313 [(2 X M- B'r ”]., 315 [I 2 X Μ-B r) Isotope] 0 β Γ-Analysis: Calculated value 10, 5 1 wt 1, Measured value 10, 42 wtl ^ 1 Η ™ NMR (( ?, Ρ P ffi, CH 3ON solvent, CH 3cn group, 22 T;): 3,00 (s, 6 Η, -CH 3 X 2), 3,92 (s, 4 Η,-C Η 2 C Η 2-) 0 13 C-NMR (δ j ppm, CH 3 C Ν solvent, DMS 0-d Β group, 22T ;) ♦ η -ί ό .5 (s, -C Η 3 x 2), 46 * 8 is,-CH 2 C Η 2-), 157.6 (d, J = 2 7 8 Η Z c- F) ° Actual Example 31 Synthesis of bromo-n-octane A ΰ; The reaction vessel was filled with (K 247 g (1 * 9 mmol) n-octanol-, 1 60 g 25 J 1 weight percent of DMFB An acetonitrile solution ((K 41 4 g, 2 * 1 mmol of DMFB) and 3 + 86 g of acetic acid, and reacted under nitrogen in a nitrogen atmosphere for 5 hours. Λ iJV Antipyrene formation edge * GC-MS measurement of the reaction mixture confirmed the formation of bromo-n-octyl (main ion 1 92, base peak 135) &lt; 3 The yield of bromo-n-octane measured by GC analysis was 98.8¾ 1 Example m 32 This paper size applies Chinese National Standard (CNS) Λ4 specification (210X297 public #) 530050 A7 V. Description of the invention () Synthesis of benzyl bromide 0.24 grams (2.0 millimoles) in a reaction vessel Stearic acid, 1.60 g of a 25.91 weight percent DMFB solution in acetonitrile (0.414 g, 2.1 mmol of DMFB in DMFB), and 3,86 g of acetonitrile, and reacted under nitrogen at room temperature for 43 hours. The results of the reaction measured by GC analysis were 11.0 «benzyl bromide, 31.5¾ benzyl fluoride, 26,0¾ benzoic anhydride, and 16.0% unreacted benzoic acid. 0 Cell Example 3 3 2- Synthesis of Fluorine_153-dimethyloxazolyl iodide (DMFI) In a 300 ml four-necked flask was charged 1 3,56 g (0.10 mol) of 2-fluoro-1 , 3-Dimethylpyrazolidine (DFI), 15 0 g (0. 10 mol) of sodium iodide, and 125 g of acetonitrile, and reacted under nitrogen in the shade for 4 hours under 25 ^. The yield of 2-fluoro-1,3-dimethyl-oxazonium iron = iodide (DMFI) was 95 «. The physical properties are as follows. FABMS; 1 1 7 [(Μ-I) +], 3 6 1 [(2 x Μ ~ I) φ] ° F- Analysis * Calculated value 2,47wU, Measured value I-analysis: Calculated value 16,38wt% Printed by the Consumers' Cooperative of the Central Bureau of Standards of the Ministry of Transportation ^ K i? 1 6, 4 1 wt S:-1 Η-NMR (δ, ppir, C Η 3 C NM, CH 3 CN, 24tn: 3.02 ( s, 6H, -CH3x 2) &gt; 3. 9 3 (s, 4 H, -CH 2 CH 2-) 〇13 C-NMR i δ ^ ppi &gt; CH3CN solvent, DMS 0-d 6 S, 24¾) : 3L6 (s,-CH3x 2), 4 6, 7 (s, ~ CH 2 CH 2-)-15 7,6 (d, J = 2 78 Hz, CF). Example 3 4 Synthesis of benzyl iodide A reaction vessel was charged with 0.216 g (2.0 mmol) of benzyl alcohol and L92 g. This paper is in accordance with the Chinese National Standard (CNS) Λ4 gauge (210X297 public expense) ... 2-iodine- 1} 3 Printed by the Consumer Cooperatives of the Central Bureau of Standards of the Ministry of Economic Affairs 530050 A7 B7 V. Description of the invention () 31.73% by weight 1) Evaluation of the ethyl diet solution (0 + 610 grams, 2.5 millimoles of DMFI) and 3.8 Gram ethyl acetate, and react under nitrogen in the shade for 5 hours at room temperature. After the reaction was completed, the benzyl iodide (main ion 218, base peak 92) was generated by GC-MS measurement of the reaction mixture. The yield of benziodide measured by GC analysis was 92,21. Practical Example 3 5 Synthesis of benzyl fluoride Fluorine was charged in a reaction vessel (K60 g (4 + 91 mmol) benzoic acid, 4 "3 g 31.73 weight percent DMFI in acetonitrile solution (1, 31 g, 5 DMPI, 36 mmol) and 3, 8 g of acetonitrile, and reacted under nitrogen at room temperature for 12 hours at room temperature. The reaction results measured by GC analysis were 35,71 benzamidine fluoride, 17.2¾ of benzoic anhydride and 40,6 «of unreacted benzoic acid. Example 36 Synthesis of methyl azole sulfonium = sulfonated hydrazone A 100 ml four-necked flask was charged with 8,45 g (0, 05 mol) of 2-chloro-1,3 ~ dimethyl_oxazonium = chloride, 29,98 g (0 * 20 mol) of iodination, and 60 ml of acetonitrile, and shielded in nitrogen The reaction was performed at 25C with 55 poems. After the reaction was completed, 500 ml of anhydrous propidium was added to the slurry-like reaction mass. The sodium iodide and the unreacted 2-chloro-1,3-dimethylamine were added. Radical_oxazonium = chloride is extracted into the organic solvent layer, and the reaction material is passed to obtain a cake of crude crystals expected to produce plums. 2-sulfo-〗, 3-dimethyl_oxazonium = iodide The crude crystals have a passivity of 6 3. 5 8 I and contain sodium chloride The physical properties are as follows: I-Analysis: Calculated value 45 * 841, Measured value 44. 9¾. 1 H-NMR &lt; δ, This paper scale applies Chinese National Standard (CNS) Λ4 gauge (210X 297 public dream) Read-first Note for reading re-order 72 530050 A7 B7 V. Description of the invention () ppm ^ D20 / CD3CN = 2/1, TMS base: 3, 19 (s, 6 Η, -CH3 x 2) ^ Central Standard of the Ministry of Economic Affairs Printed by the Bureau ’s Consumer Cooperatives 3.97 (s, 4Η, -CH2CH2 ™) 〇13 C ~ NMR (δ, ρριπ, D20 / CD3CH 2 2/1, CD3CN based): 37,7is, -CH3x 2), 5 0. 6 (-CH 2 C Η 2-) &gt; 134j (C- I) 〇 Example _ Example 37 〇 _ Fluoro-1,3-dimethyl_ oxazonium diiodide Synthesis: 00 ml A four-necked flask was charged with 19, 7 g (0,01 7 mol) of 11,7 weight percent DF I in acetonitrile, 2 ♦ 5 5 g (0, 0 1 7 mol) of sodium iodide and 10 ml of acetonitrile, and under a light-shielded condition at 25 t under nitrogen: reaction for 3 hours. Thus prepared 2-fluoro-1,3-dimethyl- 0couzole iron = iodide. Example 3 Synthesis of 8 benzyl iodide A 100 ml four-necked flask was charged with 8.45 g (0,05 mole) of 2-chloro-1,3 dimethyl-oxazoline. Dichloride, 29,98 g (0,20 mol) of iodination and 60 ml of acetonitrile, and reacted under nitrogen in the light for 25 hours at 25t. Then 5 * 4 g ((K05 mol) benzene Methanol was added to the reaction mass, and reacted under nitrogen at 60 1C for 24 hours under light shielding. After the reaction was completed, the GC-MS measurement of the reaction mixture confirmed that benzyl iodide (main ion, 218) was formed. Hidden yield is 62 1 ° Example 39 Synthesis of benzyl iodide 2-Fluoro-3-dimethyl_oxazonium_ prepared in Example 33 = sedative added 1 ♦ 2 g (0 · 01 1 Moore) Benzene ring 8 and under nitrogen in a light-shielded 25-paper scale to apply the Chinese National Standard (CNS) Λ4 specification (210X297 male f) 530050 B7 5. Description of the invention () t reaction for 24 hours. After the reaction is completed Then, GC-MS measurement confirmed that 218). The reaction yield is 901. Example 40 Synthesis of 1,3-dimethyl-2-chlorooxazolyl iron = halide (DMCI) A 100 ml four-necked reaction flask was charged with 16, 90 grams (0 "0 moles) of 2-chloro-1,3-dimethyl_azole« face = chloride, 14.99 grams ((K100 moles) of sodium iodide and 60 grams of ethyl chloride, and nitrogen The reaction was performed at room temperature for 40 hours under light-shielding, and the inorganic salt was subtracted from the reaction mixture to obtain 82.6 g of a DMCI / acetonitrile solution having a concentration of 27, 3 I. The yield of DMCI was 86 + 61.

The D M C I concentration was determined by reacting DMCI with benzylamine and measuring the amount of the derivative produced by high performance liquid chromatography. The concentration of chloride and iodide was measured by silver nitrate titration. The scanning range of G C _ M S is 5 0 0 S ^ / L ^ D0 0 The properties are as follows. Iodine content of the solution on M: calculated value 1 3, 3 $ 5 found value 1 3 — 11. The chlorine content of the solution on M: the calculated value is 3.7 I, and the measured value is 3, 8 I. 1 Η-Η Η κ (δ, ppm f C Η 3 C Ν dissolved in SI y C Η 3 CN based, 2 It)): 3 * 1 2 (s, 6 H, ~ CH 3 2) Central Bureau of Standards, Ministry of Economic Affairs Printed by the employee consumer cooperative, 4,00 (s, 4H, HCH2-:} 〇13 C-rf MR i 5, ppi ^ CH3CH solvent 5 UH 5 ύ ~ d 8 Φ ZIU;; ό 4 ♦ D \ S «~ L Π 3-· κ Z) Λ 4 y * bH s,-(; 1 (: »2»), 155,9 (3, = (:-[:] 丨. "为 15-》 5 (Mother liquor: _Nitrobenzyl alcohol &quot; UDMC bu I) +], 3 9 3 [i 2 x DMCI-I ”] 〇Cell example 41 A benzyl iodide on the A \-: Vep ^ CiC? '-; Y \: 、, ·? 一 ， ·· 八 广 ·-^ 3 * 十 十-「-T * \ + ， 十 ί * Τ ~ ί Take the reaction Gu Yi 屮 若 八 h υ δ 儿 i 9 + y δpen旲) The standard of this paper and the standard of this paper are applicable to the Chinese National Standard (CNS) Λ4 Regulation (210X297) -7 4 530050 A7 B7 V. Description of the invention () 1 1. 4 3 g 2 7, .3 weight percent solution of DMC in acetic acid (3 ", 2 g, 1 L 9 8 millimoles of DMC Π; and reacted at 60 υ for 40 hours under nitrogen and light shading. St .Reaction mixing_tGC-MS Form benzyl iodide (main ion 2 1 8 and base peak 92). The production of benzyl iodide measured by GC analysis is 8 6. 5 I. Bao Shixiang 42 Synthesis of benzyl chloride in a reaction vessel Charge; 22 grams (9.99 mmol) of benzoic acid, 11 * 43 grams of 27,3 weight percent DMCI in acetonitrile (3.12 grams, 11 * 98 mmol of DMCI), and 20.0 grams of acetonitrile, and The reaction was carried out under nitrogen and light-shielded at 60¾ for 24 hours. After the reaction was completed, GC-MS measurement and GC analysis of the reaction mixture confirmed that benzoyl chloride was produced (main ion 140, base peak 105). Benzoic anhydride (base (Peak 105) is a by-product. The yields of the reaction are 92,5¾ of benzalkonium chloride &amp; 5¾ of benzoic acid ITO ϋ Example 43 1, 3-Dimethyl-2-chlorotriazole 1,2 Synthesis of bromide (DMC Β) in a 500 ml four-necked reaction flask containing 50.00 g (0.296 mol) of manganese 2-Chloro-1, 3-dimethyl printed by the Consumer Cooperatives of the Central Standards Bureau of the Ministry of Economic Affairs Amidazolium chloride, 3 (K 86 g (0 + 300 moles) bromide) and 240 ml of acetonitrile were reacted at 80 C under nitrogen for 30 hours. The reaction mixture was hot-filtered on 70 t] M, and inorganic salts were removed. The dissolving surface was removed from the liquid to obtain a solid. Recrystallization was performed by using 0.7 ml of ethyl acetate on 1 g of the precipitated solid. The DMCB thus obtained was 37 * 5 grams of white crystal. The yield is 59, 34 «. Under the physical section. This paper scale applies the Chinese National Standard (CNS) Λ4 gauge (210 × 297 male i) _ 7 r _ 530050 A7 B7 V. Description of the invention () Bromine analysis: Calculated value 3 7. 41, measured value 3 7 + 71. Chlorine analysis Calculated 16,6¾, S Pi ® 1 6, 41-1 Η — NMR (3, ρρι, CD3CN Sol, TMS group, 21t &quot; 3,15 (s, 6H, -CH3x 2), UOisjH , -CH2CH2-) 〇13 C-NMR (5, ppm, CD3CM solvent, CD 3 C Nd e δ, 2 1 ° C): 35, 2 (s,-CH 3 x 2), 5 (K 8 (s ,-CH 2 CH 2-), 156.3 (s, = C-Cl). FABMS (mother liquor: m-nitrobenzyl alcohol): 133 [(DMCB-Brv) Printed by the Consumer Cooperatives of the Central Standards Bureau, Ministry of Economic Affairs +], 347 [Isotopes of (2 x DMCB-Br) + peak]. Example 44 Synthesis of bromo-n-octane In an ephemeris container, 1 * 30 g (9,98 mmol) n-octanol, 2.1 4 g (10, / \-Τι UL · mmol) DMC B and 50 ml of acetonitrile, and reacted at 8 4t] for 3 3 hours 0 at trans-B &amp; Γ may be completed by GC-MS of the reaction mixture Measurement confirmed the formation of bromo-n-octyl fet (base peak 55, which is consistent with the standard 圏). The reaction yield measured by GC analysis was 96% c. Example 45 Synthesis of benzyl bromide K inversion vessel Fill 1 • 0.8 g (9 j 9 mmol) of benzyl alcohol, U4 g (Π 0.02 mmol) of DMC β and 50 ml of acetonitrile 3 and invert under nitrogen at 841 C for 24 hours. After the completion of the reaction, the GO MS · amount of the reaction mixture was confirmed to form benzyl bromide (main ion 17 0, base peak 91). 〇Inverse rrfsr m measured by GC analysis. Industry Science 85 «: Shimeam am Example 46 benzene A fm fcr m —y 80% of the anti-iriy response-"τΐτ * · 1 * 22g η 3, 9 9 mol)) stupid formic acid _, 2 ″ 4g This paper size applies Chinese national standards (CNS ) Λ4 gauge (210X297). Printed by the Consumers Cooperative of the Central Standards Bureau of the Ministry of Distillation. 530050 A7 B7. 5. Description of the invention () (10.02 mmol) DMCB and 50 ml of acetonitrile, and react at 84 ° C for 24 hours. . After the reaction was completed, it was confirmed that the benzamidine chloride (main ion 140, base peak 105) and benzoic anhydride (main peak 105) were formed from the G C-M S measurement of the reaction mixture and by comparing the retention time with the G C reference substance. The reaction yield was 6 6 IR 121 ° Example 47 Synthesis of 3, 3 'difluoro-2 -methylpropionate In a 300 ml autoclave was charged L70 g (24.3 mmol) of methyl allyl Aldehyde, 55 g of acetonitrile, 6,61 g (48,6 mmol) of DFI and 10 g (99 mmol) of triethylamine, the autoclave was closed tightly after the reaction system was replaced by K nitrogen, and at 100 t : Next reaction for 5 hours. The internal pressure increased to 1.96 X 1 P a during the reaction. After cooling, a small amount of water was added to the reaction mass, and GC and GC-MS measurements were performed continuously. The results confirmed that the yield of M90I yielded 3,35-difluoro-2-methylpropane (the main ion 91) and unreacted methallylaldehyde (the main ion 7 0) were 1 0 I. Example 48 3,3 The synthesis of? -Difluoropropion is packed in a 300 ml autoclave filled with 40 g of L40 (25 mmoles) of feminaldehyde, 55 g of acetonitrile, 6 + 61 g (48.6 mmoles) of DFI, and 10 g (99 mmol), after the reaction system was replaced by M nitrogen, the autoclave was closed tightly and reacted at 100 ° C for 5 hours. The internal pressure was increased to 1 + 96 X 1 0 ^ Pa during the reaction process. Yuling 5 After adding a small amount of water to the reaction mass, continuous GC and GC-MS measurement. The results confirmed that the yield of M88I produced 3, 3'-difluoropropene (main ion 78) and unreacted methyl Yi Bing Xing (the main ion 56) is 121. This paper size is applicable to the Chinese National Standard (CNS) Λ4 gauge (210 '公 297 males) 7 7 (Read the precautions on the back before filling in this page • ^ 装 π Fill in the binding order 530050 A7 B7 V. Description of the invention () Example 49 393 夂 Synthesis of difluoropropene In a reaction vessel, 5 g (4.40 mmol) of 11% by weight DFI in acetonitrile solution and 0.2 55 (4. 40 millimolar) allyl alcohol, and reacted under nitrogen at 25 scoops for 4 hours. After completion of the reaction, GC-MS measurement of the reaction mixture confirmed that 3-fluoropropane (main ion 60) was formed The reaction yield measured by GC was 981. Example 50 Synthesis of 2-fluoroethyl methacrylate In a reaction vessel, 8 g (6.48 mmol) of 9.251 DFI in acetonitrile solution and 0.842 g ( 6,48 millimolar) 2-hydroxyethyl methacrylate, and reacted at 2 5 ° C for 2 hours. After the reaction was completed, GC-MS measurement of the reaction mixture confirmed the formation of methylpropionate 2-fluoro Ethyl ester (the main ion 132). The reaction yield measured by GC analysis is 94¾. Printed on the paper by the Consumer Standards Cooperative of the Central Standards Bureau of the Ministry of Distillation. The paper size is applicable to the Chinese National Standard (CNS) Λ4 gauge (210X 297 gf) 8

Claims (1)

530050 A8 B8 C8 D8 Red 6 To] T1 is a lower alkyl group having 2 to 4 carbon atoms, and they may be the same or different; or R1 and R3 may be bonded to form a five-membered ring or a six-membered ring including a nitrogen atom. 2. If the fluorinating agent in item 1 of the patent application scope, wherein the fluorinating agent represented by chemical formula (1) is represented by chemical formula (2): (CHa (Please read the precautions on the back before filling this page) RN \ R (2) FF printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economy, where a is an integer of 2 or 3, R5 and R6 are low-carbon alkyl groups having 1 to 4 carbon atoms, and they may be the same or different. 3. The fluorinating agent according to item 2 of the scope of patent application, wherein the fluorinating agent represented by chemical formula (2) is 2,2-difluoro-1,3-dimethylimidazolidine represented by chemical formula (3) : H3 C—NN—C H3X (3) FF 4 · As the fluorinating agent in the second item of the scope of patent application, wherein the fluorinating agent represented by the chemical formula (2) is 2,2 represented by the chemical formula (4) Difluoro-1,3 -dibutyl paper size is applicable to Chinese National Standard (CNS) A4 (210 x 297 mm) 530050 A8 B8 C8 D8 (4) VI. Application scope of patents: imidazole η-H 9C 4 —NN —C 4H 9-η XFF 5. The fluorinating agent according to item 1 of the scope of patent application, wherein the fluorinating agent represented by chemical formula (i) is a fluorinating agent. Bis-dimethylaminodifluoromethane represented by formula (6) ... (Please read the precautions on the back before filling in this page) H3C C Η \ ν Ν <H3c / χ c Η (6) F Intellectual property of the Ministry of Economic Affairs Printed by the Bureau ’s Consumer Cooperatives 6. If the fluorinating agent in the scope of patent application No. 1 is applied, the fluorinating agent represented by the chemical formula (1) is bis-di-n-butylaminodifluoro represented by the chemical formula (7) Methane: FF 7 · A method for preparing a fluorine compound represented by the chemical formula (8-1): Rn-F (S-1) wherein Rn is a substituted or unsubstituted alkyl group having 1 to 8 carbon atoms, and wherein May contain unsaturated groups, including compounds that have an alcoholic hydroxyl group and are represented by the chemical formula (S): Rn-OH (B) This paper size applies the Chinese National Standard (CNS) A4 specification (21〇 × 297 mm) 2 530050 A8 B8 C8 D8 6. Scope of patent application Among them, R11 is the same as the chemical formula (S-1), and the fluorinating agent represented by the chemical formula (1) defined in the item of the patent application · Fan ® is in the temperature range _ is β Reaction at 4ϋ to 10CTC. 8 · A method for preparing a fluorine compound represented by the chemical formula (9-1): (F) Vn -CY ^ b (9 ^ 1) where V is -N02 group, b is an integer of 1, and C is an integer of 1 'And b + CS 6, which includes a compound of phenol or thiophenol represented by chemical formula (9): (Please read the precautions on the back before filling out this page) · Consumption by employees of the Intellectual Property Bureau of the Ministry of Economic Affairs Printed by a cooperative (QH) c (9) where Q is an oxygen or sulfur atom, and Y1, b, and c are the same as the chemical formula (9 · 1), and are the same as the chemical formula (1) defined in item 1 of the scope of patent application Otherwise, the fluorinating agent is reacted in a temperature range of 0 to 150 ° C. 9. A method for preparing a fluorine compound represented by the chemical formula (10-1): R] 2 -CHF2 (10, 1) wherein R12 is an alkyl group having 1 to 6 carbon atoms, or a phenyl group, which includes the following: An aldehyde compound represented by the chemical formula (1 0): R12-CH0 (10) where R12 is the same as the chemical formula (10-1), and the fluorination is represented by the chemical formula (1) defined in item 1 of the scope of patent application. The agent reacts at a temperature range of 0 to 1 50 ° C. This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)-δ, I ϋ ϋ ϋ ϋ n ϋ I ϋ ϋ ϋ ϋ ^ 1 · ϋ n · ϋ ϋ n ϋ ϋ ι ϋ ϋ nnn ϋ I ϋ I 530050 A8 B8 C8 D8 Patent application scope 1 0 · A method for preparing a fluorine compound represented by the chemical formula (1b 1) R, 3 \ c / F R14 / \ f (11-1 where R13 and R14 are A substituted or unsubstituted alkyl group, or a substituted or unsubstituted phenyl group, and they may be the same or different; and R13 and R14 may be bonded to form a ring, which includes a ketone compound represented by the chemical formula (11): R 13 (11): c = 〇RC Please read the note on the back? Matters before filling out this page} Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs, where R13 and R14 are the same as the chemical formula (11 -1) The fluorinating agent represented by the chemical formula (1) in item 1 of the patent range is reacted at a temperature range of 0 to 15 ° C. 11. A method for preparing an acid fluoride represented by the chemical formula (12-1): R15-COF (12.1) wherein R15 is a phenyl group, which includes a carboxy compound represented by the chemical formula (12): R15-COOH (12 ) Among them, R15 is the same as the chemical formula (丨 factory 丨), and the fluorinating agent represented by the chemical formula (1) of the first patent application range is -40 to 1 001 in the temperature range: the reverse is 1 2 (1 3 -1) Fluorine compound method: (F) d &lt; Yl) b (13-1) This paper size applies to China National Standard (CNS) A4 (210 X 297 public love) 4 ί ϋ « ^ 1 ϋ ϋ I ^ 1 ϋ ϋ ϋ ^ 1 n I n 1 &gt; ϋ ^ 1 &gt; 1 ϋ ^ 1 II ϋ ϋ n ϋ ϋ 530050 A8 B8 C8 D8, where Y1 is nitro, b and d Is an integer of 1 to 5, and b + d 彡 6, which includes an aromatic compound containing a halogen atom other than fluorine and represented by the chemical formula (〗 3): (X i) d-(YOb (13) where X ! Is a national atom other than fluorine, and γ〗, b, and d are the same as the chemical formula (1 3 -1) 'and the fluorinating agent represented by the chemical formula (丨) in the first patent application range is in the temperature range. Reaction to 150 ° C. 1 3 · —A method for making fluorine-containing olefin compounds represented by chemical formula (25): R1 R ------------ (Please read the precautions on the back before Fill out this page)) C: (25 ) RZ Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs where R15 to R17 are hydrogen atoms or low-carbon alkyl groups with 丨 to 3 carbon atoms, and they may be the same or different: and Z is-(Y) n-CHF2 Or-(Y) n-CH2F, where Y is -CH2- and η is an integer of 0 or 1 to 5, which includes a fluorinating agent represented by the chemical formula (丨) in the first patent application range and a chemical formula ( 24) The silk hydrocarbon compound represented by the reaction at a temperature range of 0 to 15 R 5 5 R 1 6 (24) Order --------- line X where R 15 to is a hydrogen atom or has 1 to 3 carbons Atomic low-carbon alkyl 'and it may be the same or different ... and X is _ (Y) n_CH〇 or _ (Y) n_CH2〇H, this paper size applies Chinese national standard (CNS> A4 specification (210 X 297 public) Love) Αδ B8 C8 D8 (3) Scope of patent application where γ is 2- and η is 0 or an integer of i to 5. 14. The method as claimed in any one of claims 7 to 13, wherein the fluorinating agent is represented by the chemical formula (2) as described in claim 2. 15. — A compound represented by the chemical formula (2): (c H 2) a, 'N \ R6 (2) F p where a is an integer of 2 or 3, and R5 and R6 are those having i to 4 carbon atoms. Lower alkyl, and they may be the same or different. 16 · The compound of the 15th item in the scope of the patent application, which is represented by the chemical formula (3) 2, 2, 1-fluoro-, 3, dimethyl imidazolidine: H3 C-NN-C Η 3 XFF 17 · If the compound in the scope of the patent application No. 15 is 2,2-difluoro-i, 3-di-n-butylimidazolidine represented by the chemical formula (4): --------- ---- ΙΑ __ ^ ________ Order --------- line 丨 (Please read the precautions on the back before filling out this page) Printed by NN—C 4 H9 —η FF (4) 18. A method for preparing a fluorinating agent represented by chemical formula (i) as described in item 丨 of the patent application scope, which comprises using a compound represented by chemical formula (丨 4):, R 3 RR., + / N \ \ R 4 (14) I χ2 · χΓ The paper size is applicable to Chinese National Standard (CNS) A4 (210 X 297 mm) 6 530050! A8 1 1 B8 C8 D8 6. The scope of patent application including xa and X3 Is a chlorine or desert atom '... to V are a lower alkyl group having 1 to 4 carbon atoms, and they may be the same or different; or ... and RS may be bonded to form a ring including a nitrogen atom' and the chemical formula (14 ) Compound The scale is 2 to 5 g. The metal salt of the fluorogen is tested in a inert solvent at a temperature range of -20 to 150 ° C. The halogen exchange reaction is performed. 19 · A chemical formula (1 5) _Chemistry | j : .R 3 (15) RR) N ^ + ^ NIX 4 X5 (Please read the precautions on the back before filling out this page) f where X4 and X are halogen atoms, and both L and x5 are fluorine atoms and chlorine Other than an atom or a bromine atom 'which may be the same or different; R1 to R4 are low-carbon radicals having 1 to 4 carbon atoms and which may be the same or different; or ... and R3 may be bonded to form a nitrogen atom Ring. 20_ If the halogenating agent of item 19 in the scope of the application for a patent, wherein the halogenating agent represented by the chemical formula (1 5) is represented by the chemical formula (丨 6): N \ R χ4 χ5- where X4 and X5 are _original 'and Except that j X4 and X5 are both fluorine atom, chlorine atom or bromine atom, they may be the same or different; a is an integer of 2 or 3, and R5 and R6 are low-carbon alkane having 1 to 4 carbon atoms And they can be the same or different. 21 · If the halogenating agent in item 20 of the scope of patent application, the chemical formula of this paper applies the Chinese standard (CNS) A4 specification (210 x 297 mm) 1: mouth, a 1 n IIII ϋ II ϋ ϋ ϋ nnl I Bn κ ϋ ϋ ϋ ϋ ϋ ϋ · ϋ &lt; (C Η 2); R 6 / Printed by the Consumer Cooperative of the Intellectual Property Bureau of the Ministry of Economic Affairs (16) 530050 A8 B8 C8 D8 6. The halogenating agent represented by the scope of the patent application (16) is a group represented by the chemical formula (U) j methyl imidazoline = halide: χ4 X (17) where λ% and X5 are halogen atoms, except for L and χ5 They are all except fluorine atom, chlorine atom or bromine atom, which may be the same or different. 22 · If the _ chemical agent in the scope of the application for patent No. 20, wherein the halogenating agent represented by the chemical formula (16) is 2 ... fluorine represented by the chemical formula U 8). 3 _ dimethyl imidazoline = Chloride: H3 C—N .-; N—C Η (18) FC 2 3. The halogenating agent according to item 20 of the patent application scope, wherein the halogenating agent represented by the chemical formula (1 6) is represented by the chemical formula (1 9) Representing 2-fluoro-1,3-dimethylimidazoline = bromide: -------------------- Order ------- --Line IAWI (Please read the precautions on the back before filling this page) Printed by H3 C—N · +; N—C Η r FB r _ 19) of the Intellectual Property Bureau of the Ministry of Economic Affairs 24. If the scope of patent application The halogenating agent according to item 20, wherein the halogenating agent represented by the chemical formula (16) is 2-fluoro-1, 3-dimethylimidazolium represented by the chemical formula (20) == iodide: This paper size applies China National Standard (CNS) A4 specification (210 X 297 mm) 8 530050 A8 B8 C8 D8 VI. Patent application scope Η 3 c—N +. Ν—C Η τ FI-(20) 2 5. The halogenating agent of item 20, wherein the chemical formula (1 6) The halogenating agent is 2-chloro-1 4 3 -dimethylimidazoline key = bromide represented by the chemical formula (2 1): Η 3 C—N +. Ν—CH a C 1 B r- 26 The halogenating agent according to item 20 of the application, wherein the halogenating agent represented by the chemical formula (16) is 2-chloro-1,3-dimethylimidazoline 雠 = iodide represented by the chemical formula (2 2) : (21) (Please read the notes on the back before filling this page) Η 3 C —N.; Ν 一 C Η 3 (22) Printed by C1 27 of the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs. The halogenating agent according to item 20, wherein the halogenating agent represented by the chemical formula (1 6) is 2-iodine-1,3-dimethylimidazoline recorded by the chemical formula (2 3) = iodide: Η 3 C— Ν; Ν—C Η 3 (23) This paper size is applicable to Chinese National Standard (CNS) A4 Regulation (210 X 297 mm) 9 530050) A8 1 'B8 C8 D8 Six. Application for patent scope 28.—kind of preparation such as Method for applying halogenating agent represented by chemical formula (15) as defined in item 19 of the scope of patent application, which comprises making a compound represented by chemical formula (14) = Rl \ / R3 R2 / 2 / \ R4 (14) X 2 X a- in which X2, λ% and R1 to R4 are the same as those defined in item 18 of the scope of the patent application, and the fluorine atom and chlorine of 2 to 5 children are the same as those of the compound of formula (14) The alkali metal salt of the atom, bromine atom or iodine atom or a mixture thereof is subjected to halogen exchange reaction in an inert solvent at a temperature range of -20 to 150 ° C. 29 · —A method for preparing a halogen compound represented by the chemical formula &lt; 8-2): Rn-X5 (8-2) wherein Ru is an alkyl group having 1 to 8 carbon atoms, and an unsaturated group may be contained therein And X5 is a halogen atom, which includes an alcoholic hydroxy compound represented by the chemical formula (8): RM-OH (8) wherein R &quot; is the same as the chemical formula (8-2), and is represented by the chemical formula (1 5) The above halogenating agents are reacted at a temperature range of -40 to 100 t: R1 R3 &gt; N ·, +, N Eight R 2 / \ R 4 (15) IX 4 X 5-Among them, X4 and X5 are related to the patent application It is the same as defined in item i 9 of the scope. 30 · —A method for preparing acid halide species represented by chemical formula (12-2) The paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) (Please read the precautions on the back before filling in this Page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs — — — — — — I— 11111111 --- I-— II-— II-I--II ___ __ 10 530050 1 A8; * B8 C8 D8 VI. Patent Application Range method: R15-COX6 (12-2) where R15 is a phenyl group, and χ6 is a halogen atom represented by X4 or X5 in the chemical formula (1 5) of item 19 of the patent application scope, which includes using the chemical formula (1 2) A carboxylic acid compound represented by: R15-COOH (12) wherein R15 is the same as the chemical formula (12-2), and reacts with a halogenating agent represented by the chemical formula &lt; 15) at a temperature range of -40 to 100 ° C: ( (Please read the notes on the back before filling out this page.) I X4 Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economy, where X4, X5 and R1 to R4 are the same as those defined in item 19 of the scope of patent application. 31 · —A method for preparing a fluorine compound represented by chemical fluorene (10_2): Rl2-CH (X7) 2 (10-2) wherein R12 is phenyl 'and x7 is the chemical formula (1) in the 19th scope of the patent application The halogen atom represented by X4 or X5 in 5) is not the same as two x7, and it includes the aldehyde compound represented by the chemical formula (10). R &quot; -CHO (10) where R12 is the same as the chemical formula (10-2) It is the same as the halogenating agent represented by the chemical formula (15) at a temperature range of 0 to 150 ° C: R1, .R3., +, N (R 2 / XR 4 (15) IX 4 X5- this paper size Applicable to China National Standard (CNS) A4 specification (210 X 297 public love) 11 »nm 1» _ϋ 1§ in I aMf I ^^ 1 i ^ i ϋ · Ian i. ···· n 1 ^ 1 · ϋ 1 in ter II ϋ I 530050,, &gt; A8 B8 C8 D8 Printed by the Consumers' Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 6. The scope of patent application where X4, Xs and R1 to R4 are the same as those defined in item 19 of the scope of patent application 32 · —A method for preparing a halogen compound according to any one of claims 28 to 30 in the patent application range, wherein the halogenating agent is represented by chemical formula (1 7) Η α C —N .. N —CH 3 -r .X ·. X5 (17) where X4 and X5 are halogen atoms, except that / \ 4 and X5 are both fluorine atom, chlorine atom or bromine atom, which may be the same or different. 0 3 3 · —a compound represented by the chemical formula (1 5) ·· R 1 N &gt; N ·, + 〆] ^ R 2 / \ R 4 (15) IX 4 X5 'where X4 and X5 are _ atoms, and Except X4 &amp; X5 are all fluorine atom, chlorine atom or bromine atom, they may be the same or different: 1 ^ 1 and R4 are lower alkyl groups having 1 to 4 carbon atoms, which may be the same or different: or ... And R3 can be bonded to form a ring including a nitrogen atom or a nitrogen atom and other heteroatoms. • 3 4 · — ^ compounds of the formula Tpc represented by the chemical formula (1 6): (C Η 2) \ R 6 (16) X 4 X Γ except that X4 and X5 are both fluorine, chlorine or desert atoms, X, and X5 are the same or different halogen atoms, a is an integer of 2 or 3, V and &amp; is a lower alkyl group having 1 to 4 carbon atoms, and it may be the same or different. This paper size applies to Chinese National Standard (CNS) A4 specifications (210 X 297 mm) 12 (Please read the precautions on the back before filling out this page) 530050) A8 ί * Β8 C8 D8 VI. Patent application scope 3 5. The halogenating agent in the scope of application for item 19, wherein the halogenating agent is a 2- -yl-1,3-dimethylimidazoline represented by the chemical formula (1 7) = halide: Η 3 C —N, + ; Ν—C Η 3 (17) X 4 X 5 where X4 and X5 are the same as above. 3 6. — A compound represented by the chemical formula (1 8) Imidazoline = chloride: 2-fluoro-1,3-dimethyl (please read the precautions on the back before filling this page) Η 3 C Ν + .N —CH r FC 1-(IS) 3 7 * —A compound represented by the chemical formula (1 9), 2.-Fluoro-1,3-dimethylimidazoline = bromide: (19) FB r Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs 3 8.—A compound represented by the chemical formula (20), 2-fluoro-1,3-dimethylimide π sitting morpholine = iodide: H3 CN N—CH3 (20) F 39 · — A compound represented by the chemical formula (21), 2-chloro-1 / 3 -dimethylimidazoline 鏠 = bromide: — · ϋϋ i i ί n I ον I mn ϋ i ^ i ϋ 1 · ϋ I i ^ in ϋ κ κ ϋ la ϋ BmMm ϋ ϋ n — ^ 1 ϋ i ϋ —i II · ϋ m &gt; 1 i This paper size applies to China National Standard (CNS) A4 specification (210 X 297 mm) 13 530050 A8 B8 C8 D8 6. Application scope Η 3 CN +. Ν—C Η Cl Br- (21) 40 · —A compound represented by the chemical formula (22), 2-chloro-1, 3 Imidazoline gun = Iodide: H3 CN +. N—C Η r c 1 1 (22) 41 · A compound represented by the chemical formula (23), 2-iodo-1,3 · dimethylimidazolium = iodide: Η 3 C -N. + · Ν ——C Ηr (23) 42 * —A method for preparing a halogenating agent represented by the chemical formula (1 5) (Please read the precautions on the back before filling this page) Printed by Rl \ / R3 from the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs R2 / XR 4 IX 4 x5 a (15) where X4 and Xs are halogen atoms, and except that X4 and x5 are each a fluorine atom, a chlorine atom, or a bromine atom 1 which may be the same or different; R1 and R4 are those having 1 to Low-carbon alkyl group with 4 carbon atoms, and they can be the same or different: or R3 This paper size is applicable to China National Standard (CNS) A4 (210 X 297 mm) 14 530050 A8 B8 C8 D8 Bonding to form a ring including a nitrogen atom, which includes a compound represented by the formula (1): R 1 R &gt; N N &lt; ^ X \ RFF (1) wherein R1 to R4 are the same as above, and are the same as those of chlorine, bromine or The alkali metal salt of an iodine atom is subjected to a halogen exchange reaction in the presence of a solvent at a temperature range of -20 to 150 ° C. (Please read the notes on the back before filling out this page) Printed by the Consumer Cooperatives of the Intellectual Property Bureau of the Ministry of Economic Affairs t ------- --Order --------- Line I ------ ----------------- 15 This paper size applies to China National Standard (CNS) A4 (210 X 297 mm)