Method for preparing 4-cypro methylene phenylboronic acid

A technology of cyclopropyl methylene benzene boronic acid and cyclopropyl methylene chlorobenzene, applied in the field of preparing 4-cyclopropyl methylene benzene boronic acid, can solve the problem of low yield, high price of bromobenzene, and unsuitability for large-scale industrialization Problems such as producing 4-cyclopropyl methylene benzene boronic acid, to achieve the effect of reducing preparation cost and low cost

Inactive Publication Date: 2017-07-28
BENGBU CHINA SYNCHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The price of bromobenzene as a raw material is relatively high, and the yield is low, so it is not suitable for large-scale industrial production of 4-cyclopropylidenephenylboronic acid

Method used

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  • Method for preparing 4-cypro methylene phenylboronic acid

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] (1) Friedel-Crafts acylation reaction: 10L glass reactor equipped with mechanical stirring and thermometer, under the protection of nitrogen, add 1000g of chlorobenzene and 1000g of 4-chlorobutyryl chloride, cool to -5°C, add trichloride in batches under stirring Aluminum 1042g, after the reaction is complete, add the system to 10L of ice water, extract and separate layers with n-hexane, concentrate the organic layer to dryness, and recover chlorobenzene with an oil pump, leaving 4-chlorobutyrylchlorobenzene as the residue.

[0026] (2) Ring closure reaction: 20L glass reactor equipped with mechanical stirring and thermometer, add 6720g of ethanol under nitrogen protection, add 1440g of sodium hydroxide in batches under stirring, cool down to below 20°C after dissolving and add 4-chlorobutyryl dropwise Chlorobenzene, after dropping, keep warm overnight. The system was distilled under reduced pressure at 60°C until there was no solvent, water and n-hexane were added to e...

Embodiment 2

[0030] (1) Friedel-Crafts acylation reaction: a 10L glass reactor equipped with a mechanical stirrer and a thermometer, add 5000g of chlorobenzene and 1000g of 4-chlorobutyryl chloride under nitrogen protection, cool down to -5°C, and add the acylating reagent in batches under stirring 1042g of aluminum trichloride, after the reaction is completed, add the system to 10L of ice water, extract and separate layers with n-hexane, concentrate the organic layer to dryness, and recover chlorobenzene with an oil pump, and the residue is 4-chlorobutyryl chlorobenzene.

[0031] (2) Ring closure reaction: 20L glass reactor equipped with mechanical stirring and thermometer, add 6720g of ethanol under nitrogen protection, add 1440g of sodium hydroxide in batches under stirring, cool down to below 20°C after dissolving and add 4-chlorobutyryl dropwise Chlorobenzene, after dropping, keep warm overnight. The system was distilled under reduced pressure at 60°C until there was no solvent, water...

Embodiment 3

[0035] (1) Friedel-Crafts acylation reaction: 10L glass reactor equipped with mechanical stirring and thermometer, under the protection of nitrogen, add 5000g of chlorobenzene and 1000g of 4-chlorobutyryl chloride, cool to -5°C, add acylating reagent in batches under stirring 1042g of aluminum trichloride, after the reaction is completed, add the system to 10L of ice water, extract and separate layers with n-hexane, concentrate the organic layer to dryness, and recover chlorobenzene with an oil pump, and the residue is 4-chlorobutyryl chlorobenzene.

[0036](2) Ring closure reaction: 20L glass reactor equipped with mechanical stirring and thermometer, add 6720g of ethanol under nitrogen protection, add 1440g of sodium hydroxide in batches under stirring, cool down to below 20°C after dissolving and add 4-chlorobutyryl dropwise Chlorobenzene, after dropping, keep warm overnight. The system was distilled under reduced pressure at 60°C until there was no solvent, water and n-hexa...

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Abstract

The invention discloses a method for preparing a 4-cypro methylene phenylboronic acid, and relates to the technical field of organic synthesis. The chlorobenzene is taken as the starting material, is subjected to a friedel-crafts reaction to generate 4-butanoyl chloride chlorobenzene, is subjected to a ring-closure reaction to generate 4-cypro formyl chlorobenzene, is subjected to a reduction reaction to generate 4-cypro methylene chlorobenzene, and is finally subjected to a Grignard boric acid reaction to generate the 4-cypro methylene phenylboronic acid. The cheap chlorobenzene, which is easy to get, is taken as the starting material, the preparation cost is remarkably lowered, the total molar yield of the product of 4-cypro methylene phenylboronic acid prepared through the 4-cypro methylene phenylboronic acid, the ring-closure reaction, the reduction reaction and the Grignard boric acid reaction is more than 35%, the production of the product is guaranteed on the basis of the low cost, and the method is suitable for industrial production.

Description

[0001] Technical field: [0002] The invention relates to the technical field of organic synthesis, in particular to a method for preparing 4-cyclopropylidene phenylboronic acid. [0003] Background technique: [0004] 4-Cyclopropylmethylene phenylboronic acid is an important molecular fragment for the preparation of new drugs for the treatment of diabetes, and it is also an important organic synthetic medicine and pesticide intermediate. The key intermediate of biphenyl compounds. Therefore, it is of great significance to develop a high-efficiency, low-cost synthesis process for 4-cyclopropylidene phenylboronic acid. [0005] At the present stage, the method for preparing 4-cyclopropanemethylene boronic acid mainly takes bromobenzene and 4-chlorobutyryl chloride as raw materials [Schliemann:Buege: Reppel:Phanmazie:Vol.35:nb,3:(1980):p 140 -143], under low temperature conditions, first Friedel-Crafts acylation reaction, then cyclization at room temperature, then high temperat...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 杨青赵士民徐剑霄黄开明
Owner BENGBU CHINA SYNCHEM TECH CO LTD
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