JPS62258332A - Production of 4-bromo-2,5-dichlorophenol - Google Patents
Production of 4-bromo-2,5-dichlorophenolInfo
- Publication number
- JPS62258332A JPS62258332A JP61100859A JP10085986A JPS62258332A JP S62258332 A JPS62258332 A JP S62258332A JP 61100859 A JP61100859 A JP 61100859A JP 10085986 A JP10085986 A JP 10085986A JP S62258332 A JPS62258332 A JP S62258332A
- Authority
- JP
- Japan
- Prior art keywords
- dichlorophenol
- bromo
- bromine
- reaction
- group
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- HWWKEEKUMAZJLL-UHFFFAOYSA-N 4-bromo-2,5-dichlorophenol Chemical compound OC1=CC(Cl)=C(Br)C=C1Cl HWWKEEKUMAZJLL-UHFFFAOYSA-N 0.000 title claims abstract description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 13
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 10
- RANCECPPZPIPNO-UHFFFAOYSA-N 2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC=C1Cl RANCECPPZPIPNO-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052740 iodine Inorganic materials 0.000 claims abstract description 3
- 239000000126 substance Substances 0.000 claims abstract 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical group OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 12
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 abstract description 10
- 229910000042 hydrogen bromide Inorganic materials 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 4
- 150000001412 amines Chemical class 0.000 abstract description 2
- 230000000694 effects Effects 0.000 abstract description 2
- 231100000053 low toxicity Toxicity 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract description 2
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 description 8
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical class ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- -1 n- Propyl Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 1
- KLCVUAIAILGDAR-UHFFFAOYSA-N 3-bromo-2,5-dichlorophenol Chemical compound OC1=CC(Cl)=CC(Br)=C1Cl KLCVUAIAILGDAR-UHFFFAOYSA-N 0.000 description 1
- ROLMZTIHUMKEAI-UHFFFAOYSA-N 4,5-difluoro-2-hydroxybenzonitrile Chemical compound OC1=CC(F)=C(F)C=C1C#N ROLMZTIHUMKEAI-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N tetrahydropyridine hydrochloride Natural products C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/52—Improvements relating to the production of bulk chemicals using catalysts, e.g. selective catalysts
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
農薬、医薬および染料等の製造中間体として有用な−４
−ブロモー２，５−ジクロロフェノールの製造法に関す
る。[Detailed Description of the Invention] [Industrial Application Field] -4 useful as an intermediate in the production of agricultural chemicals, medicines, dyes, etc.
- A method for producing bromo-2,5-dichlorophenol.
２．５−ジクロロフェノールに対し、はぼ０．５倍モル
の臭素を使用した後、副生ずる臭化水素を利用Ｌ”？：
、４−７’ロモー２，５−ジクロロフェノールを製造す
る方法には、塩素ガスを作用させる特公昭５０−７０６
５号公報記載の方法が知られている。After using about 0.5 times the mole of bromine for 2.5-dichlorophenol, the by-product hydrogen bromide is used.
The method for producing 4-7' lomo-2,5-dichlorophenol is described in Japanese Patent Publication No. 50-706, in which chlorine gas is applied.
A method described in Publication No. 5 is known.
４−ブロモー２，５−ジクロロフェノールを製造すべく
特公昭５０−７０６５号公報記載の方法に従い製造を試
みた。An attempt was made to produce 4-bromo-2,5-dichlorophenol according to the method described in Japanese Patent Publication No. 7065/1983.
その結果、トリクロロ体の副生を抑制するためには塩素
ガスの導入条件を厳密に規定しなければならないことが
わかった。As a result, it was found that in order to suppress the by-product of trichloride, the conditions for introducing chlorine gas must be strictly regulated.
また、この方法によると毒性が高く、高圧のため取り扱
いが固難である塩素ガスを使用しなくてはならず、これ
らのことは工業生産上致命的な欠点となる。Furthermore, this method requires the use of chlorine gas, which is highly toxic and difficult to handle due to its high pressure, which is a fatal drawback in industrial production.
したがって、副反応を起こさず、取り扱いが容易な酸化
剤を発見することは、４−プａモー２，５−ジクロロフ
ェノールを大量に生産する上で極めて重要な問題となる
。Therefore, finding an oxidizing agent that does not cause side reactions and is easy to handle is an extremely important problem in producing 4-poumo-2,5-dichlorophenol in large quantities.
２．５−ジクロロフェノールを臭素化して４−ブロモ−
２．５−ジクロロフェノールを製造するにあたり、副生
する臭化水素を有効に利用するために又目的物を高収率
で得るためには臭素を添加したのち、毒性が低くかつ取
り扱いが容易な過酸化水素を作用させれば良好な結果が
得られることが判明した。2. Bromination of 5-dichlorophenol to produce 4-bromo-
When producing 2.5-dichlorophenol, in order to effectively utilize hydrogen bromide as a by-product and to obtain the desired product in high yield, after adding bromine, a compound with low toxicity and easy handling is added. It has been found that good results can be obtained by using hydrogen peroxide.
以下本発明の詳細な説明する。The present invention will be explained in detail below.
本発明で用いる臭素の量は好ましくは２，５−ジクロロ
フェノールに対し０．４〜ｏ、６倍モｂテ１）ルが、０
．４８〜０．５２倍モルが特に好ましい。又過酸化水素
の量は２，５−ジクロロフェノールに対し好ましくは０
．４〜０・６倍モルであるが、０・４８〜０．５２倍モ
ルが特に好ましい。またこの過酸化水素は例えば３０％
の水溶液にして用いるのが好ましい。The amount of bromine used in the present invention is preferably 0.4 to 0.0 to 2,5-dichlorophenol;
．． Particularly preferred is 48 to 0.52 times the mole. The amount of hydrogen peroxide is preferably 0 to 2,5-dichlorophenol.
．． The amount is 4 to 0.6 times by mole, but 0.48 to 0.52 times by mole is particularly preferred. Also, this hydrogen peroxide is, for example, 30%
It is preferable to use it as an aqueous solution.
本発明で用いる反応溶媒は、反応に関与しない溶媒であ
れば特に制限はない。しかし、ヘキサン。The reaction solvent used in the present invention is not particularly limited as long as it does not participate in the reaction. But hexane.
ヘプタン等の脂肪族炭化水素類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、ジクロロメタン、クロ
ロホルム、四基化炭１ １ｔ２−ジクロロエタン、
１，１．１−トリクロロエタン等ｔ７：ｊ ハａゲン化
脂肪族炭化水素類、モノクロロベンセン。Aliphatic hydrocarbons such as heptane, benzene, toluene,
Aromatic hydrocarbons such as xylene, dichloromethane, chloroform, tetracarbohydrate 1 1t2-dichloroethane,
1,1.1-trichloroethane etc. t7:j Halogenated aliphatic hydrocarbons, monochlorobenzene.
０−ジクロロベンゼン等のハロゲン化芳香族炭化水素類
と硫酸水溶液との混合溶媒が好ましい。A mixed solvent of a halogenated aromatic hydrocarbon such as 0-dichlorobenzene and an aqueous sulfuric acid solution is preferred.
溶媒の使用量は特に制限はないが、２，５−ジクｃＩＣ
Ｉフェノールの重量に対し、有機溶媒および硫酸水溶液
はそれぞれ１ないし４倍容量使用するのが好ましい。硫
酸水溶液の濃度も特に制限はないが、６０ないし８０％
のものを使用するのが好ましい。There is no particular restriction on the amount of solvent used, but 2,5-di-cIC
It is preferable to use the organic solvent and the sulfuric acid aqueous solution in an amount of 1 to 4 times the weight of the phenol. There is no particular limit to the concentration of the sulfuric acid aqueous solution, but it is 60 to 80%.
It is preferable to use
反応温度は０℃から反応溶媒の沸点の範囲で行いうるが
、０ないし８０℃が好ましい。The reaction temperature may range from 0°C to the boiling point of the reaction solvent, preferably from 0 to 80°C.
反応時間は反応温度により変化するが、３ないし２０時
間が好ましい。The reaction time varies depending on the reaction temperature, but is preferably 3 to 20 hours.
また１本発明は一般式
〔式中、Ｒｌｙ ”２１ Ｒ３１Ｒ４はそれぞれ水素原
子。In addition, one aspect of the present invention is the general formula [wherein Rly "21 R31R4 are each a hydrogen atom.
低級アルキル基（Ｒ１，Ｒ２，Ｒ３及びＲ４のうちの任
意の２つが４又は５ケのメチレン鎖をつくり窒素原子と
共に環状となっていても良い）、７クロアルキル基また
はベンジル基を示す゛。又は塩素原子、臭素原子、ヨウ
素原子または硫酸水素基を示す。〕
で表わされるアミン誘導体の塩の存在下でも実施するこ
とにより目的物の収率、純度を上げることもできる。It represents a lower alkyl group (any two of R1, R2, R3 and R4 may form a 4 or 5 methylene chain and form a ring together with the nitrogen atom), a 7-chloroalkyl group or a benzyl group. Alternatively, it represents a chlorine atom, a bromine atom, an iodine atom, or a hydrogen sulfate group. ] It is also possible to increase the yield and purity of the target product by conducting the reaction in the presence of a salt of the amine derivative represented by the formula.
ここで低級アルキル基としては、メチル、エチル、ｎ−
プロピル、イングロビル、ｎ−ブチル。Here, lower alkyl groups include methyl, ethyl, n-
Propyl, inglovir, n-butyl.
イソブチル基などがあげられ、シクロアルキル基として
はシクログロビル、ククロプテル、シクロペンチル又は
シクロヘキシル基などがあげられる。Examples of the cycloalkyl group include isobutyl group, and examples of the cycloalkyl group include cycloglovir, cuclopter, cyclopentyl, and cyclohexyl group.
本発明の製造法により、同一の反応機内で、副反応を起
こすことなく、シかも取り扱いのために特別な装置を必
要とすることなく、副生ずる臭化水素を有効に再利用で
きるようになる。The production method of the present invention makes it possible to effectively reuse by-produced hydrogen bromide in the same reactor without causing side reactions or requiring special equipment for handling. .
つぎに、実施例により本発明の詳細な説明する。 Next, the present invention will be explained in detail with reference to Examples.
実施例１
２．５−ジクロロフェノール１２．２５ｆ（７５，Ｏｍ
ｍｏｌ ）を反応容器に取り、モノクロロベンゼン２２
Ｉｌｔを加え撹拌下溶解し、７０％硫酸水溶液２３ａｌ
ｔ−加え、５〜１０℃に冷却する。冷却後。Example 1 2.5-dichlorophenol 12.25f (75, Om
Take 22 mol of monochlorobenzene into a reaction vessel.
Add Ilt and dissolve with stirring, and add 70% sulfuric acid aqueous solution 23al
t-add and cool to 5-10°C. After cooling.
臭素６．Ｑ５ｆ（５７・ｑ ｍｍｏｌ ）を１時間かけ
て添加し、ついで３０％過酸化水素水溶液４・２９ｆ（
３７，８ｍｍｏｌ ）を１時間かけて添加した後２０〜
３０℃で２００時間反応せる。Bromine6. Q5f (57·q mmol) was added over 1 hour, and then 30% hydrogen peroxide aqueous solution 4·29f (
After adding 37.8 mmol) over 1 hour, 20~
React at 30°C for 200 hours.
反応後、有機溶媒層を分液する。水層にモノクロロベン
ゼン２０ａｌを加え十分混合した後、静置し、有機溶媒
層を分液し、１回目に分液した液と合わせる。この有機
溶媒層を水２０ ｔｉｅを使用し。After the reaction, the organic solvent layer is separated. After adding 20 al of monochlorobenzene to the aqueous layer and thoroughly mixing, the mixture is allowed to stand, and the organic solvent layer is separated and combined with the first separated liquid. This organic solvent layer was separated using 20 ties of water.
２回洗浄する。Wash twice.
水洗後、有機溶媒層を減圧下、内温９０℃以下で濃縮す
る。ついで、水３０ｄを加え、冷却し、結晶化させる。After washing with water, the organic solvent layer is concentrated under reduced pressure at an internal temperature of 90° C. or lower. Then, 30 d of water is added, cooled, and crystallized.
２０℃で濾過し、水洗後、乾燥し。Filter at 20°C, wash with water, and dry.
４−ブロモ−２，５−ジクロロフェノール１８．１Ｏｆ
を得る。純度８８．７％。収率８８．５％。4-bromo-2,5-dichlorophenol 18.1Of
get. Purity 88.7%. Yield 88.5%.
融点６７〜６９℃。Melting point 67-69°C.
実施例２
２．５−ジクロロフェノール１２．２３７（７５，０ｍ
ｍｏｌ ）を反応容器に取り、モノクロロベンゼン２２
ｆｆｉ／を加え撹拌下溶解し、トリエチルアミン塩酸塩
１．０３９ （７，５ｍｍｏｌ ） を加える。ついで
実施例１と同様にして、７０チ硫酸水溶液、臭素および
３０％過酸化水素水溶液を加え、２０〜３０℃で３時間
反応させる。Example 2 2.5-dichlorophenol 12.237 (75.0 m
Take 22 mol of monochlorobenzene into a reaction vessel.
ffi/ is added and dissolved under stirring, and 1.039 (7.5 mmol) of triethylamine hydrochloride is added. Then, in the same manner as in Example 1, a 70% aqueous sulfuric acid solution, bromine, and a 30% aqueous hydrogen peroxide solution were added, and the mixture was reacted at 20 to 30°C for 3 hours.
反応後、実施例１と同様に後処理を行い、４−ブロモ−
２，５−ジクロロフェノール１８．２２ｐを得る。After the reaction, post-treatment was carried out in the same manner as in Example 1, and 4-bromo-
18.22 p of 2,5-dichlorophenol are obtained.
純度９３．７％、収率９４．１％。融点６９〜７１℃。Purity 93.7%, yield 94.1%. Melting point 69-71°C.
実施例３
実力例２において、７０％硫酸水溶液の代わりに、８０
チ硫酸水溶液１４ｄｆ：使用し、同様に反応および後処
理を行い、４−ブロモ−２，５−ジクロロフェノール＋
８．＋６７を得る。Example 3 In Performance Example 2, 80% sulfuric acid aqueous solution was used instead of 70% sulfuric acid aqueous solution.
Thisulfuric acid aqueous solution 14df: Used and subjected to the same reaction and post-treatment to obtain 4-bromo-2,5-dichlorophenol+
8. Gain +67.
純度９２．５％。収率９２．６％。融点６８〜７０℃。Purity 92.5%. Yield 92.6%. Melting point 68-70°C.
実施例４
実施例２において、モノクロロベンゼンの代ワりにジク
ロロメタンを使用し、同様に反応および後処理を行い、
４−ブロモー２，５−ジクロロフェノール１８．２ｏｒ
を得る。純度９５．４％。収率９５．７％。Example 4 In Example 2, dichloromethane was used instead of monochlorobenzene, and the reaction and post-treatment were carried out in the same manner.
4-bromo 2,5-dichlorophenol 18.2or
get. Purity 95.4%. Yield 95.7%.
融点７０〜７２℃。Melting point 70-72°C.
実施例５
実施例２において、トリエチルアミン塩酸塩の代わりに
、ピペリジン塩酸塩０．９ ＋ ７ （７，５ｍｍｏｌ
）を使用し、同様に反応および後処理を行い、４−ブロ
モー２，５−ジクロロフェノール１８．０８ｐを得る。Example 5 In Example 2, piperidine hydrochloride 0.9 + 7 (7.5 mmol
), and the reaction and post-treatment are carried out in the same manner to obtain 18.08p of 4-bromo-2,5-dichlorophenol.
純度９２．３％。収率９２．０％。Purity 92.3%. Yield 92.0%.
融点６８〜７０℃。Melting point 68-70°C.
Claims (2)
ロモ−２，５−ジクロロフェノールを製造するにあたり
、臭素を添加した後、過酸化水素を作用させることを特
徴とする、４−ブロモ−２，５−ジクロロフェノールの
製造法。(1) In producing 4-bromo-2,5-dichlorophenol by brominating 2,5-dichlorophenol, 4-bromo-2,5-dichlorophenol is produced by adding bromine and then reacting with hydrogen peroxide. Method for producing 2,5-dichlorophenol.
低級アルキル基（Ｒ＿１Ｒ＿２Ｒ＿３及びＲ＿４のうち
の任意の２つが４又は５ケのメチレン鎖をつくり窒素原
子と共に環状となつていてもよい）、シクロアルキル基
又はベンジル基を示す。Ｘは塩素原子、臭素原子、ヨウ
素原子または硫酸水素基を示す。〕で示される化合物の
存在下臭素化を行なう特許請求の範囲第１項記載の方法
。(2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ [I] [In the formula, R_1, R_2, R_3 and R_4 are hydrogen atoms,
Indicates a lower alkyl group (any two of R_1R_2R_3 and R_4 may form a 4 or 5 methylene chain and form a ring with a nitrogen atom), a cycloalkyl group, or a benzyl group. X represents a chlorine atom, a bromine atom, an iodine atom or a hydrogen sulfate group. ] The method according to claim 1, wherein the bromination is carried out in the presence of a compound represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61100859A JPS62258332A (en) | 1986-05-02 | 1986-05-02 | Production of 4-bromo-2,5-dichlorophenol |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61100859A JPS62258332A (en) | 1986-05-02 | 1986-05-02 | Production of 4-bromo-2,5-dichlorophenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62258332A true JPS62258332A (en) | 1987-11-10 |
Family
ID=14285037
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61100859A Pending JPS62258332A (en) | 1986-05-02 | 1986-05-02 | Production of 4-bromo-2,5-dichlorophenol |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62258332A (en) |
-
1986
- 1986-05-02 JP JP61100859A patent/JPS62258332A/en active Pending
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