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Preparation method of 2,6-dibromo-4-trifluoromethoxyaniline

A technology of trifluoromethoxyaniline and fluoromethoxyaniline, applied in the field of fine chemical product preparation, can solve the problems of high bromine unit consumption, large amount of waste water, unfavorable environmental protection and the like, and achieve the effect of low bromine unit consumption

Inactive Publication Date: 2019-02-26
DALIAN QIKAI MEDICAL TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In CN1043127, the reaction of p-trifluoromethoxyaniline and bromine to prepare 2,6-dibromo-4-trifluoromethoxyaniline has the disadvantage of high cost;
[0004] In CN102491910, CN103570566, CN107540561, prepare 2,6-dibromo-4-trifluoromethoxyaniline with p-trifluoromethoxyaniline and bromine / hydrogen peroxide reaction, although the unit consumption of bromine is relatively low, the amount of waste water is relatively low Big, not conducive to environmental protection
[0005] In CN106631839, 2,6-dibromo-4-trifluoromethoxyaniline is prepared by reacting p-trifluoromethoxyaniline with sodium bromate / sulfuric acid / hydrogen peroxide. Big, bad for the environment
[0006] In other relevant documents, the introduction of the synthesis of 2,6-dibromo-4-trifluoromethoxyaniline by bromination of trifluoromethoxyaniline and bromine is the most, but all fail to solve the partial consumption of bromine. High problem, at the same time there is no introduction of the method of using p-trifluoromethoxyaniline and bromine chloride to synthesize 2,6-dibromo-4-trifluoromethoxyaniline

Method used

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  • Preparation method of 2,6-dibromo-4-trifluoromethoxyaniline

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 208g of chloroform and 43.3g of bromine into a 250ml four-necked bottle, cool down to -5°C, feed 17.5g of chlorine gas, and add the obtained chloroform solution of bromine chloride dropwise at 35°C into a 44.6g 76 g of 2,6-dibromo-4-trifluoromethoxyaniline was obtained after stirring for 12 hours in a reaction kettle containing p-trifluoromethoxyaniline and 25.4 g of triethylamine. (yield 90%)

Embodiment 2

[0025] Add 210g of 1,2-dichloroethane and 43.3g of bromine to a 250ml four-necked bottle, cool down to -5°C, and feed 17.5g of chlorine gas to dissolve the resulting bromine chloride in 1,2-dichloroethane Add dropwise at 35°C into a reaction kettle containing 44.6g of p-trifluoromethoxyaniline and 25.4g of triethylamine, keep stirring for 12 hours, filter and distill to remove the solvent to obtain 2,6-dibromo-4 - Trifluoromethoxyaniline 74 g. (yield 87.6%)

Embodiment 3

[0027] Add 356g of chloroform and 74g of bromine into a 500ml four-necked bottle, cool down to -8°C, feed 30g of chlorine gas, and drop the obtained bromine chloride solution in chloroform into a container containing 76.3g of trichloromethane at 40°C. In a reaction kettle of fluoromethoxyaniline and 34g of pyridine, heat-preserved and stirred for 16 hours, filtered and distilled to remove the solvent, 125g of 2,6-dibromo-4-trifluoromethoxyaniline was obtained. (yield 86.5%)

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Abstract

The invention relates to a preparation method of 2,6-dibromo-4-trifluoromethoxyaniline, and belongs to the field of preparation of fine chemical engineering products. The preparation method of 2,6-dibromo-4-trifluoromethoxyaniline comprises the following steps: dissolving trifluoromethoxyaniline and bromine chloride in an organic solvent, and in the presence of an acid-binding agent, reacting at the temperature of 0-80 DEG C to obtain 2,6-dibromo-4-trifluoromethoxyaniline. The molar ratio of the trifluoromethoxyaniline, the bromine chloride and the acid-binding agent is 1: 2: 1. By the method, raw materials are easily obtained, and are low in price, unit consumption of bromine is reduced effectively, the production cost is lowered, wastewater is decreased, and the method has important significance on implementation of large-scale production of the compound.

Description

technical field [0001] The invention belongs to the field of preparation of fine chemical products, and in particular relates to a preparation method of 2,6-dibromo-4-trifluoromethoxyaniline. Background technique [0002] 2,6-Dibromo-4-trifluoromethoxyaniline is an important pesticide, pharmaceutical and liquid crystal material intermediate, which is used to synthesize the agricultural insecticide Thiofuramide, and has a wide range of applications and development prospects , the domestic and foreign public technology has the following reports: [0003] In CN1043127, the reaction of p-trifluoromethoxyaniline and bromine to prepare 2,6-dibromo-4-trifluoromethoxyaniline has the disadvantage of high cost; [0004] In CN102491910, CN103570566, CN107540561, prepare 2,6-dibromo-4-trifluoromethoxyaniline with p-trifluoromethoxyaniline and bromine / hydrogen peroxide reaction, although the unit consumption of bromine is relatively low, the amount of waste water is relatively low Big,...

Claims

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Application Information

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IPC IPC(8): C07C217/84C07C213/08
CPCC07C213/08C07C217/84
Inventor 蒋斌张洪学姜殿平
Owner DALIAN QIKAI MEDICAL TECH