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Preparation method of 2-cyano-4'-bromomethylphenylbenzene

A technology of bromomethyl biphenyl and methyl biphenyl is applied in the field of preparation of 2-cyano-4'-bromomethyl biphenyl, and can solve the problems of unsuitability for production needs, poor process stability, and cost of production raw materials High problems, to achieve the effect of low cost, high active bromine content and economical use

Active Publication Date: 2014-07-02
TAINING SHENGDA INDAL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The NBS bromination method also has the following deficiencies: (1) carbon tetrachloride and dichloroethane are usually used as solvents, and carbon tetrachloride and dichloroethane are a class of solvents that are prohibited in pharmaceutical synthesis and are not suitable for Production needs; (2) AIBN or BPO is usually used as the initiator, the reaction mechanism is similar to free radical reaction, the process stability and controllability are not good during the scale-up production process; (3) The cost of production raw materials is relatively high

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] A preparation method of 2-cyano-4'-bromomethylbiphenyl, comprising the following steps:

[0016] ①In the reactor, add 1 mol of 2-cyano-4'-methylbiphenyl, 0.6 mol of dibromohydantoin, 12 mol of tetrachloroethylene, and then add 0.012 mol of catalyst benzyltriethylammonium bromide and mix Uniform;

[0017] ② Heating to react, the reaction temperature is controlled between 60-110°C, and the reaction time is 8 hours;

[0018] ③ After the reaction, cool, filter, concentrate and recover tetrachlorethylene, and then recrystallize with ethanol to obtain 2-cyano-4'-bromomethylbiphenyl with a content of 99.1%, and the reaction yield is 82.3%.

Embodiment 2

[0020] A preparation method of 2-cyano-4'-bromomethylbiphenyl, comprising the following steps:

[0021] ①In the reactor, add 1 mol of 2-cyano-4'-methylbiphenyl, 0.5 mol of dibromohydantoin, and 8 mol of tetrachloroethylene, and then add the catalyst cetyltrimethylammonium bromide 0.008 mol and mix well;

[0022] ② Heating to react, the reaction temperature is controlled between 60-120°C, and the reaction time is 4 hours;

[0023] ③ After the reaction, cool, filter, concentrate and recover tetrachlorethylene, and then recrystallize with methanol to obtain 2-cyano-4'-bromomethylbiphenyl with a content of 99.2%, and the reaction yield is 85.5%.

Embodiment 3

[0025] A preparation method of 2-cyano-4'-bromomethylbiphenyl, comprising the following steps:

[0026] ①In the reactor, add 1 mol of 2-cyano-4'-methylbiphenyl, 0.525 mol of dibromohydantoin, 10 mol of tetrachloroethylene, and then add 0.01 mol of catalyst tetrabutylammonium bromide and mix well ;

[0027] ② Heating to react, the reaction temperature is controlled between 90-110°C, and the reaction time is 6 hours;

[0028] ③ After the reaction, cool, filter, concentrate and recover tetrachlorethylene, and then recrystallize with isopropanol to obtain 2-cyano-4'-bromomethylbiphenyl with a content of 99.3%, and the yield is 88.6%.

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PUM

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Abstract

The invention provides a preparation method of 2-cyano-4'-bromomethylphenylbenzene, which comprises the following steps: (1) adding 2-cyano-4'-methylphenylbenzene, dibromohydantoin and tetrachloroethylene into a reactor, adding a catalyst, and evenly mixing, wherein the mol ratio of 2-cyano-4'-methylphenylbenzene to dibromohydantoin to tetrachloroethylene to catalyst is 1:(0.5-0.6):(8-12):(0.008-0.012), and the catalyst is tetrabutyl ammonium bromide, cetyl trimethyl ammonium bromide or benzyl triethyl ammonium bromide; (2) heating to react, wherein the reaction temperature is controlled at 60-120 DEG C, and the reaction time is controlled at 4-8 hours; and (3) after the reaction finishes, cooling, filtering, concentrating to recover the tetrachloroethylene, and recrystallizing with methanol or ethanol or isopropanol to obtain the 2-cyano-4'-bromomethylphenylbenzene. The production process provided by the invention has the advantages of high operation safety, simple technique, low cost and high yield.

Description

technical field [0001] The invention relates to the technical field of preparation of 2-cyano-4'-bromomethyl biphenyl, in particular to a preparation method of 2-cyano-4'-bromomethyl biphenyl. Background technique [0002] 2-cyano-4'-bromomethylbiphenyl is the main intermediate in the synthesis of sartan drugs. The traditional synthesis methods of 2-cyano-4'-bromomethylbiphenyl mainly include bromine bromination method and NBS bromination method. The bromine bromination method needs to use bromine in production, the production operation is more dangerous, there are safety problems, and the utilization rate of bromine is not high. The NBS bromination method also has the following deficiencies: (1) carbon tetrachloride and dichloroethane are usually used as solvents, and carbon tetrachloride and dichloroethane are a class of solvents that are prohibited in pharmaceutical synthesis and are not suitable for Production requirements; (2) AIBN or BPO is usually used as the initia...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C255/50C07C253/30
CPCY02P20/584
Inventor 张小兵江戈华王昇鹰陈胜林汪家良梁智宏
Owner TAINING SHENGDA INDAL
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