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Preparation method of benzbromarone

A technology of benzbromarone and hydroxyphenyl, applied in the field of preparation of benzbromarone, can solve the problems of strong bromine corrosivity, pollute the environment, great harm to human body, etc. good effect

Active Publication Date: 2021-03-09
常州康普药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In order to solve the technical problems that bromine is used to carry out bromination reaction in the last step of bromination reaction of benzbromarone in the prior art, bromine is highly corrosive, harmful to human body and pollutes the environment, the invention provides a The preparation method of benzbromarone

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] (1), the preparation of 4-methoxyphenyl-(2-ethyl-3-benzofuryl) ketone

[0025] Add 1.4kg of p-methoxybenzoyl chloride to the reaction kettle, add 1kg of 2-ethylbenzofuran and 8.84kg of dichloromethane, then cool to a temperature ≤ 5°C, and add 1 molar equivalent of polystyrene-loaded aluminum trichloride (prepared by existing published literature method), stirred at room temperature for 1 hour, added water layer, and the water layer was extracted twice with dichloromethane, combined extracts, respectively with 10% mass concentration of sodium hydroxide solution, 10% mass concentration of Wash each with hydrochloric acid once, then wash with saturated brine until neutral, dehydrate with anhydrous sodium sulfate, and concentrate the dichloromethane extract. Cool the concentrated solution to below 10°C, precipitate crystals, filter, wash twice with absolute ethanol, filter dry, cool to crystallize, filter, and dry to obtain 4-methoxyphenyl-(2-ethyl-3-benzofuran Base) keto...

Embodiment 2

[0033] (1), the preparation of 4-methoxyphenyl-(2-ethyl-3-benzofuryl) ketone

[0034] Add 1.4kg of p-methoxybenzoyl chloride to the reactor, add 1kg of 2-ethylbenzofuran and 9kg of dichloromethane, then cool to a temperature ≤ 5°C, add 1 molar equivalent of polystyrene-loaded aluminum trichloride, Stir at room temperature for 1 hour, add water to separate layers, extract the water layer twice with dichloromethane, combine the extracts, wash with 10% mass concentration of sodium hydroxide solution and 10% mass concentration of hydrochloric acid once respectively, and then wash with saturated brine Wash until neutral, dehydrate with anhydrous sodium sulfate, and concentrate the dichloromethane extract. Cool the concentrated solution to below 10°C, precipitate crystals, filter, wash twice with absolute ethanol, filter dry, cool to crystallize, filter, and dry to obtain 4-methoxyphenyl-(2-ethyl-3-benzofuran Base) ketone, yield 98%.

[0035] (2), the preparation of 4-hydroxypheny...

Embodiment 3

[0042] (1), the preparation of 4-methoxyphenyl-(2-ethyl-3-benzofuryl) ketone

[0043]Add 1.4kg of p-methoxybenzoyl chloride to the reactor, add 1kg of 2-ethylbenzofuran and 8kg of dichloromethane, then cool to a temperature of ≤5°C, add 1.5 molar equivalents of polystyrene-loaded aluminum trichloride, and Stir for 1 hour, add water to separate layers, extract the water layer twice with dichloromethane, combine the extracts, wash with 10% mass concentration of sodium hydroxide solution, 10% mass concentration of hydrochloric acid, and then wash with saturated brine To neutrality, dehydrate with anhydrous sodium sulfate, and concentrate the dichloromethane extract. Cool the concentrated solution to below 10°C, precipitate crystals, filter, wash twice with absolute ethanol, filter dry, cool to crystallize, filter, and dry to obtain 4-methoxyphenyl-(2-ethyl-3-benzofuran Base) ketone, yield 97.8%.

[0044] (2), the preparation of 4-hydroxyphenyl-(2-ethyl-3-benzofuryl) ketone

[...

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PUM

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to a preparation method of benzbromarone. According to the method disclosed by the invention, polystyrene-loaded aluminum trichloride is used as a catalyst to carry out Friedel-Crafts acylation reaction, so that the catalytic effect is good, and the catalyst can be recycled, in the demethylation reaction process, aluminum trichloride is adopted to replace common pyridine hydrochloride, so that the reaction temperature can be reduced, and the yield can be increased, in the bromination reaction, sodium sulfide and hydrogen peroxide are adopted to replace bromine, so that the technical problems of strong corrosivity of bromine, great harm to human bodies and environmental pollution are solved, and meanwhile, the yield can be further improved.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of benzbromarone. Background technique [0002] Benzbromarone (benzbromarone) is a benzofuran derivative, its chemical name is: (3,5-dibromo-4-hydroxyphenyl) (2-ethyl-3-benzofuranyl) ketone, which is White or almost white crystalline powder, insoluble in water, slightly soluble in ethanol. It is a drug for the treatment of simple primary hyperuricemia and non-attack gouty arthritis. [0003] In the conventional preparation method of benzbromarone, in the last step of the bromination reaction, bromine is used to carry out the bromination reaction, but bromine is highly corrosive, harmful to the human body, and pollutes the environment. Contents of the invention [0004] In order to solve the technical problems that bromine is used to carry out bromination reaction in the last step of bromination reaction of benzbromarone in the prior ...

Claims

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Application Information

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IPC IPC(8): C07D307/80
CPCC07D307/80Y02P20/584
Inventor 殷晓伟王姝汤金春
Owner 常州康普药业有限公司
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