JPS63270644A - Novel dichlorotrifluoromethylnitrotoluene and production thereof - Google Patents

Abstract

NEW MATERIAL:Dichlorotrifluoromethylnitrotoluene (with the proviso that 2-nitro-3,4-dichloro-6-trifluoromethyltoluene is omitted). USE:A raw material for drugs and agricultural chemicals. Especially useful as a raw material for methylaminobenzotrifluoride as an intermediate raw material for herbicide. PREPARATION:Dichlorotoluene is reacted with CCl4 in the presence of an aluminum halide at 20-80 deg.C for 20min-4hr to give dichlorotrichloromethyltoluene, which is reacted with >=theoretical amount of HF in a stainless steel autoclave at room temperature - 100 deg.C under 8-10kg/cm<2> for 3-6hr to give dichlorotrifluoromethyltoluene, which is reacted with fuming nitric acid in the presence of conc. sulfuric acid to give the aimed substance.

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention provides a novel dichlorotrichloromethylnitrotoluene ( (hereinafter abbreviated as DCTFNT) and its manufacturing method.

[Prior art] As a method for producing methylaminobenzotrifluoride,
The following are known:

σ, 8. P., 44132737 (1979)B
e1g, BE 899927 (1984) However, the production method of (1) uses expensive 3-trifluoromethyl-benzyl alcohol as a starting material;
SF4 as a fluorinating agent in the production method I) is difficult to obtain in large quantities, is expensive and highly toxic, and has problems such as being reacted at high temperature and high pressure. Furthermore, the method for producing (III) also had the problem of using expensive 3-trifluoromethyl-toluene as a starting material.

[Means for Solving the Problems] In the process of studying an advantageous method for producing methylaminobensitrifluoride, the present inventor discovered a novel compound that is extremely excellent as a raw material for its production, and thus arrived at the present invention. That is, the present invention is a novel dichlorotrifluoromethylnitrotoluene (excluding 2-dichloro-3,4-dichloro-trifluoromethyl-toluene) and a method for producing the same,
The production method is a method for producing dichlorotrifluoromethylnitrotoluene, which is characterized by nitrating dichlorotrifluoromethyltoluene (excluding 3,4-dichloro-6-trifluoromethyltoluene).

Dichlorotrifluoromethyltoluene (DCTPT), which is a raw material for this reaction, can be easily obtained by fluorinating dichlorotrichloromethyltoluene (DCTCT) with carbon tetrachloride in the presence of aluminum halide.

Examples of the aluminum halide include anhydrous aluminum chloride and anhydrous aluminum bromide, and the amount of aluminum halide used is 1 to 6 mol, preferably 1 to 3 mol, based on dichlorotoluene as the raw material. Aluminum halide forms a complex with DCTCT, so when aluminum halide is insufficient, dichlorobis(dichloromethylphenyl)methane (hereinafter referred to as DCBM) is used.
A by-product called ) is selectively produced. Furthermore, the selectivity of DCTCT does not increase even if aluminum halide is used in excess.

The reaction temperature of this reaction is 0 to 100°C, preferably 20 to 80°C.

In addition, it is preferable to use a solvent in this reaction, and examples of the solvent that can be used include methylene chloride, tetrachloroethane, and fluorocarbons, but 1,2-dichloroethane is a solvent that can significantly improve the selectivity of DCTCT. The most preferable zero reaction time cannot be unconditionally defined, but is 20 minutes to 4 hours. Water is added to the reaction product thus obtained to decompose the complex,
Obtain DCTCT.

The fluorination reaction of DCTCT involves placing DCTCT and more than the theoretical amount of hydrogen fluoride in a stainless steel autoclave.
It is carried out at a temperature of 0 to 150°C, preferably room temperature to 100°C. In addition, the reaction pressure is 3 to 20 kg/d, preferably 8
It is carried out at ~10 kg/-. The amount of hydrogen fluoride is preferably 3.2 to 12 times mole relative to DCTCT.
The 0 reaction time, which is 6 to 9 times the mole, cannot be absolutely defined, but the 0 reaction product, which is 3 to 6 hours, is washed with an alkaline aqueous solution and then distilled under reduced pressure to remove the reaction solvent, unreacted carbon tetrachloride, Furthermore, by removing high-boiling reaction products, highly pure dichlorotrifluoromethyltoluene (hereinafter referred to as DCTPT) can be easily obtained.

The DCTPT thus obtained was reacted with fuming nitric acid in the presence of concentrated sulfuric acid to produce dichloronitrotrifluoromethyltoluene (dichloronitrotrifluoromethyltoluene), which is the target compound of the present invention.
DCTFNT) is generated. 96-98 in this reaction
The amount of concentrated sulfuric acid to be used is 3 to 6 times the mole of DCTPT, and the amount of 94% fuming nitric acid to be used is 1 to DCTPT.
~2 times the mole, preferably 1.05 to 1.20 times the mole. Moreover, the reaction temperature of this reaction is preferably in the range of 30 to 120°C, more preferably 60 to 100°C.

Although the reaction time cannot be absolutely specified, it is 2 to 5 hours. In this reaction, the position where the nitro group is introduced is 2,
6 for 3-dichloro-4-trifluoromethyltoluene
position it, 4 position in 2,3-cyclo-6-trifluoromethyltoluene, 5 position in 2゜4-dichloro-5-trifluoromethyltoluene, and 5 position in 2,5-dichloro-4-trifluoromethyltoluene. selectively introduced at position 6.

The present invention will be explained in detail below using examples.

Reference example 1 Anhydrous aluminum chloride 27.0g (0,203 mol)
A mixed solution of 16.1 g (0.1 mol) of 2゜3-dichlorotoluene (0.1 mol) and 54 g of carbon tetrachloride (total 1.0 mol) was added under stirring to a mixed solution of 100.0 g of carbon tetrachloride.
The mixture was added dropwise at 52°C for 2 hours, and the mixture was stirred and reacted for an additional 2 hours. After cooling, the reaction solution was poured into 700 val of ice water and stirred at room temperature to remove aluminum chloride. The aqueous layer was extracted with carbon tetrachloride, and the collected organic layer was washed with an aqueous sodium hydroxide solution, dried over anhydrous calcium chloride, and the solvent was distilled off under reduced pressure to obtain 24.5 g of crude DCTCT. When this was analyzed by gas chromatography, 2,3-dichloro-4-trichloromethyltoluene (DCTCT■) was found to be 42.8%.
(yield 37.6%), 2.3-dichloro-6-trichloromethyltoluene (DCTCT■) was 27.1 wt%
(yield 23.8%) and dichlorobis(2,3-dichloro-4-methylphenyl)methane and dichlorobis(2-methyl-3,4-dichlorophenyl)methane (D
CB M) was contained in an amount of 30.14% (yield 36.6%), and unreacted dichlorotoluene was not detected. After adding 725.2 g of crude DCTC to 50 ml of n-hexane and removing undissolved substances, the liquid was concentrated under reduced pressure and distilled under reduced pressure to obtain DCTCT■+DCT with a purity of 99.2%.
CT■10.5g (0,0377mol, yield 37.7
%) was obtained. From this, using gas chromatography, DCTCT■ with a purity of 99.5% (boiling point 120-125℃
/3mmHg) and 99.0% purity
DCTCT ■ (boiling point 109~1) 5℃/3 mdg
) was separated into 0.12 g. The structure of DCTCT■ is shown in the mass spectrum (M+276) and H-NMR spectrum (CDCl solvent, 62.80 3H (CHs)
S, 7.99IH (5-H) S, 7.38
Confirmed by 1H(6-H)S).

The structure of DCTCT■ is shown in the mass spectrum (M"276"
), H-NMR spectrum (C001g solvent, δ2
．． 47 31((CHI)S, 7.22 1H(4-
H)S,? .

90 18 (5-H) S).

Reference example 2 Anhydrous aluminum chloride 108 g (0,812 mol)
, and 125 g (0,812 mol) of carbon tetrachloride, and 1
．． In a mixed solution of 205 g of 2-dichloroethane, under stirring,
A mixed solution of 65.4 g (0,406 mol) of 2゜3-dichlorotoluene and 78.0 g of 1゜2-dichloroethane was added dropwise at 50 to 52°C over 30 minutes, stirred for another 2 hours, and left to cool, then poured into ice water. The same operation as in Reference Example 1 was performed except for pouring the reaction solution into 10100O, and crude DCTCT102
I got g. When this was analyzed by gas chromatography, DCTCT■ was 51.5 wt% (yield 46.8%)
, DCTCT■ is 30.4 wt% (yield 27.6%)
and DCBM were contained in an amount of 18.5% (yield 27.6%), and unreacted 2,3-dichlorotoluene was not detected.

Reference example 3 Anhydrous aluminum chloride 27.0g (0,203 mol)
A mixed solution of 16.1 g (0.1 mol) of 2°4-dichlorotoluene and 54 g (total 1.0 mol) of carbon tetrachloride was added under stirring into a mixed solution of ioo, o g of carbon tetrachloride.
The mixture was added dropwise at 52°C for 2 hours, and the mixture was stirred and reacted for an additional 2 hours. After cooling, the reaction solution was poured into 700 ml of ice water and stirred at room temperature to remove aluminum chloride. The aqueous layer was extracted with carbon tetrachloride, and the collected organic layer was washed with an aqueous sodium hydroxide solution, dried over anhydrous calcium chloride, and the solvent was distilled off under reduced pressure to obtain 24.3 g of crude DCTCT. When this was analyzed by gas chromatography, 2,4-dichloro-5-trichloromethyltoluene was found to be 70.2 wt% (yield 61.3%).
), DCBM was contained at 29.8 wt% (yield 35.9%), and unreacted dichlorotoluene was not detected.

After adding 724.3 g of crude DcTc to 50 ml of n-hexane and removing undissolved substances, the limbs were concentrated under reduced pressure and distilled under reduced pressure to obtain 713.8 g of DCTC with a purity of 98.7% (
0,0496 mol, yield 49.6%) was obtained (melting point 79
．． 0-80.2°C). The structure is mass spectrum (M”27
3), H-NMR spectrum (CDCIs solvent, δ
2.60 H(CH3)5,7.72 1H(6
-H)S, 8°21 1H(3-H)).

Reference example 4 Anhydrous aluminum chloride 27.0g (0,203 mol)
and 31.5 g (0,205 mol) of carbon tetrachloride; 1.
In a mixed solution of 50.5 g of 2-dichloroethane, under stirring,
2゜4-dichlorotoluene 16.1g (0.1 mol)
The same operation as in Reference Example 3 was performed except that a mixed solution of 19.1 g of 1,2-dichloroethane and 1,2-dichloroethane was added dropwise.
CT24.3g (purity 70.2%, yield 61.3%)
I got it. Unreacted 2,4-dichlorotoluene was not detected in this crude DCTCT, and DCBM was detected as a by-product.
only was detected.

Reference example 5 Anhydrous aluminum chloride 27.0g (0,203 mol)
A mixed solution of 16.1 g (0.1 mol) of 2°5-dichlorotoluene and 54 g (total 1.0 mol) of carbon tetrachloride was added under stirring to a mixed solution of 100.0 g of carbon tetrachloride and 100.0 g of carbon tetrachloride.
The mixture was added dropwise at 52°C for 2 hours, and the mixture was stirred and reacted for an additional 2 hours. After cooling, the reaction solution was poured into 1000 ml of ice water and stirred at room temperature to remove aluminum chloride. The aqueous layer was extracted with carbon tetrachloride, the collected organic layer was dried over anhydrous calcium chloride, and the solvent was distilled off under reduced pressure to obtain 24.1 g of crude DCTCT. When this was analyzed by gas chromatography, 2.5-dichloro-4-trichloromethyltoluene was found to be 72.1wt.
% (yield: 62.4%), DCBM was contained at 27.94% (yield: 33.3%), and unreacted dichlorotoluene was not detected.

725.5 g of crude DCTC and 50 ml of fi'% xane
In addition, after removing undissolved substances, the limbs were concentrated under reduced pressure and distilled under reduced pressure to obtain DCTCTll, 5 with a purity of 99.2%.
g (0,0410 mol, yield 41.0%) (melting point 41.6-42.5°C), whose structure was determined by mass spectrometry (M
"273"), H-NMR spectrum (CDCI,
Solvent, 62.39 )1 (CH,) S, ? ,
40 1H (3-H) S, 8゜13 1H (6-H
Confirmed by ``)S'').

Reference example 6 Anhydrous aluminum chloride 27.0g (0,203 mol)
,! -Tetrachlorinated carbonff131.5g (0,205-t-
16.1 g of 2゜5-dichlorotoluene (
The same operation as in Reference Example 5 was performed except that a mixed solution of 0.1 mol) and 19.1 g of 1,2-dichloroethane was added dropwise to obtain 25.2 g of crude DCTCT (purity 78.8%, yield 71.3%). I got it. Unreacted 2,5-dichlorotoluene was not detected in this crude DCTCT, and only DCBM was detected as a by-product.

Reference example 7 Anhydrous aluminum chloride 27.0g (0,203 mol)
and 31.5 g (0,205 mol) of carbon tetrachloride and 1.2
- Into a mixed solution of 50.5 g of dichloroethane, 2.
16.1 g (0.1 mol) of 6-dichlorotoluene and 1
．． 2-dichloroethane19. Ig mixed solution 50-5
The mixture was added dropwise at 2° C. over 2 hours, and the mixture was stirred and reacted for an additional 2 hours.

After cooling, the reaction solution was poured into 1000 ml of ice water and stirred at room temperature to remove aluminum chloride. The aqueous layer was extracted with carbon tetrachloride, and the collected Arfi was washed with an aqueous sodium hydroxide solution, dried over anhydrous calcium chloride, and the solvent was distilled off under reduced pressure to obtain 26.0 g of crude DCTCT. Analysis of this by gas chromatography revealed that 2,6-dichloro-3-
Trichloromethyltoluene is 88.4 wt% (yield 82
．． 7%), DCBM7!1<1). 6wt% (yield 1
5.0%) and unreacted DCT was not detected.

Reference Example 8 102 g of crude DCTCT obtained in Reference Example 2 and 109 g of hydrogen fluoride were placed in a 300+*1 stainless steel autoclave and stirred while heating at a reaction temperature of 95 to 100°C, so that the reaction pressure was 3 kg/cIa. Hydrogen chloride gas, a side reaction product, was continuously extracted from the upper part of the reflux column using a primary pressure HM valve.

After 3 hours, when no rise in reaction pressure was observed, the fluorination was judged to have been completed, and the reaction product was taken out of the autoclave and washed with an aqueous sodium hydroxide solution to remove unreacted hydrogen fluoride. Purity 9 by distilling under reduced pressure
7.42 g of 8.3% 2゜3-dichloro-4-trifluoromethyltoluene (hereinafter referred to as DCTFT) (
0,0319 mol, yield 16.6%, boiling point 1)5-1)
8°C/35mmHg) with a purity of 99.2%.
Dichloro-6-trifluoromethyltoluene (hereinafter referred to as DC
7゜45 g (0,0323 mol,
Yield 28.3%, boiling point 108~1) 0℃/35mmH
g) was obtained. The structure of DCTFT■ is + mass spectrum (M 228 ), H-NMR spectrum (CDCl 3 solvent, δ2.48 3H (CHI
) S, 7°24 18 (6-H) S, 7.
52 1H(5-H)S), F-NMR spectrum (
CDC1g solvent, 61.5ppm 3F (CFm)S
Confirmed using reference material CFCII).

Similarly, the structure of DCTFT■ has mass spectrum + (M228'), H-NMR spectrum (CD
C1m solvent, 62.583H(CHs)S, 7.
48 28(4,5-H)S), F-NMR spectrum (CDC1s solvent, 63.3ppa+3F (CFi
) S, reference material CFCI, ) was confirmed.

Reference Example 9 724.3 g of crude DCTC obtained in Reference Example 3 and 10.0 g of hydrogen fluoride were placed in a 100+nl stainless steel autoclave and stirred while heating at a reaction temperature of 95 to 102°C until the reaction pressure was 8 kg/cd. Hydrogen chloride gas, a side reaction product, was continuously extracted from the upper part of the reflux column using a primary pressure regulating valve.

After 3 hours, when no rise in reaction pressure was observed, it was judged that the fluorination was complete, and the reaction product was taken out of the autoclave, washed with an aqueous sodium hydroxide solution to remove unreacted hydrogen fluoride, and then distilled under reduced pressure. Purity 9
12.3 g of 8.2% 2°4-dichloro-5-trifluoromethyltoluene (0,0527 mol, yield 86
．． 0%, boiling point 83-85°C/6+I1 mHg). The structure is mass spectrum (M228), H-NM
R spectrum/L/ (CDCIs solvent, δ2゜363H
(CHI) S, 7.43 1) 1(6-H) S,
7.50IH(3-H)S), F-NMR spectrum (CDC1m solvent, 62.8ppm 3F(CF
Confirmed by S), reference material CFCIs).

Reference Example 10 724.1 g of crude DCTC obtained in Reference Example 5 and 10.0 g of hydrogen fluoride were placed in a 100 ml stainless steel autoclave and stirred while heating at a reaction temperature of 95 to 102°C, resulting in a reaction pressure of 8 kg/cj. Hydrogen chloride gas, a side reaction product, was continuously extracted from the upper part of the reflux column using a primary pressure regulating valve.

After 3 hours, when no rise in reaction pressure was observed, it was judged that the fluorination was complete, and the reaction product was taken out of the autoclave, washed with an aqueous sodium hydroxide solution to remove unreacted hydrogen fluoride, and then distilled under reduced pressure. Purity 9
7.8% 2°5-dichloro-4-trifluoromethyltoluene 1). 3g (0,0483 mol, yield 77.
3%, boiling point 83-85°C +/5 mmHg). The structure is mass spectrum (M
228), H-NMR spectrum (CDCI” solvent, δ2゜353H'(CHs)S, 7.32
18(3-H)S, 7.61)H(6-H)S
), (F-N?lR spectrum (CDCIg solvent, 63, ippm 3F (CFs) S, reference material CFCIs).

Reference Example 1) Crude DCTCT26 obtained in Reference Example 7. Og and hydrogen fluoride 1
0.0g was charged into a 100ml stainless steel autoclave and stirred while heating at a reaction temperature of 95 to 102°C.
Hydrogen chloride gas, a side reaction product, was continuously extracted from the upper part of the reflux column using a primary pressure regulating valve so that the reaction pressure was 8 kg/-. After 3 hours, when no rise in reaction pressure was observed, it was judged that fluorination had been completed, and the reaction product was taken out of the autoclave, washed with an aqueous sodium hydroxide solution to remove unreacted hydrogen fluoride, and then distilled under reduced pressure. By doing this, 2.6-dichloro-3- with a purity of 98.7% was obtained.
Trifluoromethyltoluene 16.6g (0,0527
Mol, yield 87.8%, boiling point 83-85℃/8mm1g
) was obtained. The structure is mass spectrum (M”228)
, H-NMR spectrum (CDC1m solvent, δ2.58
31) (CHs ”) S, 7.33 18
(5-H)S, 7.43IH(4-)1)
S), F-NMR spectrum (CDC1m solvent, 62
．． 8ppa+ 3F (CFs) S, reference material C
Confirmed by FCIs).

Example 1 7.42 g of DCTFT obtained in Reference Example 8 (0°0
319 moles) and 16.3 g of 96% concentrated sulfuric acid (0,160
moles) and 2.60 g of 94% fuming nitric acid (0,038
8 mol) was placed in a glass round-bottomed flask, and stirred and reacted at a reaction temperature of 80° C. for 1 hour under normal pressure. After the reaction was completed, 30 g of 1,2-dichloroethane was added and dissolved as a solvent, and the organic layer separated into two layers was washed with a sodium hydroxide solution to remove the acid content. 1,2-dichloroethane was removed by distillation from the organic layer using an evaporator, and the purity was 97.8.
% DCTFNT ■ 8.28 g (0,0296 mol,
2.3-dichloro-4-trifluoromethyl-6-nitrotoluene (DCTFNT) with a purity of 99.2% was obtained by recrystallization with n-hexane (yield 92.7%).
(melting point 44.5-45.7°C). The structure is shown in the mass spectrum (M”273) and H-NMR spectrum (C
DC1m solvent, 62.1731 ((CH)S, 8.
04 1H(5-H)S), F-NMR spectrum (CDCI! Solvent, 63.8 ppm 3F (CFI
)S.

Confirmed using reference material CFCI, ').

Example 2 DCTFT obtained in Reference Example 8 7.45g <0°0
323 moles) and 16.5 g of 96% concentrated sulfuric acid (0,162
mole), and 94% fuming glass &2.60g (0,0
38) was placed in a glass round-bottomed flask, and stirred and reacted at a reaction temperature of 80° C. for 1 hour under normal pressure. After the reaction was completed, 30 g of 1,2-dichloroethane was added and dissolved as a solvent, and the organic layer separated into two layers was washed with a sodium hydroxide solution to remove the acid content. 1,2-dichloroethane was distilled off from the organic layer using an evaporator to obtain a purity of 98.
9% 2,3-dichloro-6-trifluoromethyl-4
-Ditrotoluene (DCTFNT■) 8.36g (
0,0302 mol, yield 93.4%) was obtained. Then n
-DCTFN of 99.1% purity by recrystallization with hexane
To obtain T■, melting point 25.5-27+, 0°C). The structure is mass spectrum (M 273), H
-NMRx hector (CDC1g solvent, δ0.483
) [(CHI) S, 5.87 1H (5-H)
S), F-NMRxhex) (CDCI” solvent, 6
2. lppm 3F (CFs) S, reference material CF
Confirmed by CI, ).

Example 3 14.3 g of D CT P T obtained in Reference Example 9 (
0,0616 mol), 31.4 g of 96% concentrated sulfuric acid (0,
308 mol) and 4.95 g of 94% fuming nitric acid (0,
0738 mol) was placed in a glass round-bottomed flask, and stirred and reacted at a reaction temperature of 80° C. for 1 hour under normal pressure. After the reaction was completed, 30 g of 1,2-dichloroethane was added as a solvent and dissolved, and the organic layer separated into two layers was washed with a sodium hydroxide solution to remove the acid content, dried over anhydrous calcium chloride, and then evaporated into 1.2-dichloroethane using an evaporator. 2-dichloroethane was removed by distillation to obtain 2゜4-dichloro-3- with a purity of 97.8%.
Nitro-5-trifluoromethyltoluene 16.2g
(0,0578 mol, yield 93.9%) was obtained. Then, DCTF with a purity of 99.5% was obtained by recrystallization with n-hexane.
NT was obtained (melting point 58.1-58.8°C). The structure is mass spectrum (M”273), H-NMR spectrum (CDC1m solvent, 62,493H(CHs)S
, 7.68 1H(6-H)S') ,F-N
MR spectrum (CDCI, solvent, 61.3 ppm 3
F (CFs) S, reference material 'CFCI,'')
Confirmed by.

Example 4 13.6 g of D CT P T obtained in Reference Example 10
, 29.4 g (0,289 mol) of 96% concentrated sulfuric acid and 4.64 g (0,0692 mol) of 94% fuming nitric acid were placed in a glass round-bottom flask, and the reaction temperature was 80° C. under normal pressure.
The mixture was stirred and reacted for 1 hour. After the reaction is completed, as a solvent 1.
After adding and dissolving 30 g of 2-dichloroethane, the organic layer separated into two layers was washed with a sodium hydroxide solution to remove the acid content. 1.2-dichloroethane was removed by distillation from the organic layer using an evaporator to obtain 2.5-dichloroethane with a purity of 98.2%.
Dichloro-4-trifluoromethyl-6-nitrotoluene 15.4 g (0,0552 mol, yield 95.7%)
The obtained 0 was then recrystallized with n-hexane to a purity of 99.
2% DCTFNT was obtained (melting point 48.5-49.4°C
), structure is mass spectrum (M+273'), H-N
MR spectrum (CDCI! Solvent, δ2.413H (C
HI)S, 7.85 1)(34)S), F-NM
R spectrum (CDC1m solvent, 63.2ppm 3F
Confirmed using (CFs)81 reference material CFCIg>.

Example 5 16.6 g of D CT P T obtained in Reference Example 1)
(0,0715 mol), 96% concentrated sulfuric acid 36.5 g (0
, 358 mol) and 5.75 g of 94% fuming nitric acid (0
, 0,858 mol) was placed in a glass round-bottomed flask, and stirred and reacted at a reaction temperature of 80° C. for 1 hour under normal pressure. After the reaction was completed, 50 g of 1,2-dichloroethane was added and dissolved as a solvent, and the organic layer separated into two layers was washed with a sodium hydroxide solution to remove the acid content. 1,2-dichloroethane was removed by distillation from the organic layer using an evaporator to obtain a purity of 9.
18.9 g (0,0674 mol, yield 94.2%) of 7.5% 2,6-dichloro-3-trifluoromethyl-5-nitrotoluene was obtained by recrystallization with n-hexane. DCTFNTe with a purity of 99.5% was obtained (melting point 4
0.7-41.5℃), the structure is mass spectrum (M”
273), H-NMR spectrum (CDCl.

Solvent, 62.6831) (CH,) S, 8.0
7 1H(3-H)S), F-NMR spectrum (
CDCI, solvent, 63.7 ppm 3F (CF, )
Confirmed by S, reference material CFCI, ).

[Effects of the Invention] The novel dichlorotrifluoromethyltoluene of the present invention can be easily and easily produced and is extremely useful as a raw material for producing aminotrifluoromethyltoluene derivatives useful as intermediates for medicines and agricultural chemicals.

Patent applicant: Central Glass Co., Ltd. Agent: Patent attorney: Eiji Sakamoto, '(7:

Claims (2)

[Claims] (1) Dichlorotrifluoromethylnitrotoluene (excluding 2-nitro-3,4-dichloro-6-trifluoromethyltoluene). (2) Dichlorotrifluoromethyltoluene (however, 3
, 4-dichloro-6-trifluoromethyltoluene).