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Preparation method of 2-bromo-4(4-ethoxyphenyl) oxazole

A technology of ethoxyphenyl and oxazole is applied in the field of novel preparation of pharmaceutical intermediates and can solve problems such as difficulty in synthesis

Inactive Publication Date: 2015-01-07
湖南华腾制药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis of 2-bromo-4(4-ethoxyphenyl)oxazole is difficult at present

Method used

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  • Preparation method of 2-bromo-4(4-ethoxyphenyl) oxazole
  • Preparation method of 2-bromo-4(4-ethoxyphenyl) oxazole
  • Preparation method of 2-bromo-4(4-ethoxyphenyl) oxazole

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Embodiment 1

[0022] (1) Synthesis of 1-(4-ethoxyphenyl)-2-hydroxyethanone

[0023] Add 50g of 2-bromo-1-(4-ethoxyphenyl)ethanone to 600ml of ethanol, add 100ml of water and 80g of sodium hydroxide, heat and reflux for 20 hours, cool, concentrate and then add ethyl acetate, and separate the layers , dried, concentrated, and the residue was subjected to column separation to obtain 29 g of 1-(4-ethoxyphenyl)-2-hydroxyethanone.

[0024] (2) Synthesis of carbamic acid-(1-(4-ethoxyphenyl)-2-hydroxyethanone) ester

[0025] Add 51g of N,N-dimethylaniline to 220ml of toluene, add 110ml of 1.9M phosgene toluene solution, cool to 0°C, add 28g of 1-(4-ethoxyphenyl)-2-hydroxyethanone, Stir for 30 min, add 600 ml of ammonia water, stir for 1 h, filter, collect the filter cake, and dry to obtain 32 g of carbamic acid-(1-(4-ethoxyphenyl)-2-hydroxyethanone) ester.

[0026] (3) Synthesis of 4-(4-ethoxyphenyl)oxazol-2-(3H)-one

[0027] Add 30g of carbamic acid-(1-(4-ethoxyphenyl)-2-hydroxyethanone) ester ...

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Abstract

The invention discloses a preparation method of 2-bromo-4(4-ethoxyphenyl) oxazole. According to the method, 2-bromo-1-(4-ethoxyphenyl) ethanone is taken as a starting raw material and is subjected to hydrolysis, esterification, cyclization and bromination to obtain a target product. The compound is an important medical intermediate.

Description

technical field [0001] The invention relates to a novel preparation method of a pharmaceutical intermediate, in particular to a preparation method of 2-bromo-4(4-ethoxyphenyl)oxazole. technical background [0002] Compound 2-bromo-4 (4-ethoxyphenyl) oxazole, the structural formula is: [0003] [0004] The compound 2-bromo-4(4-ethoxyphenyl)oxazole and related derivatives are widely used in medicinal chemistry and organic synthesis. The synthesis of 2-bromo-4(4-ethoxyphenyl)oxazole is relatively difficult at present. Therefore, it is necessary to develop a synthetic method with easy-to-obtain raw materials, convenient operation, easy-to-control reaction and suitable overall yield. Contents of the invention [0005] The invention discloses a method for preparing 2-bromo-4(4-ethoxyphenyl)oxazole, which uses 2-bromo-1-(4-ethoxyphenyl)ethanone as the starting material and undergoes Hydrolysis, esterification, ring closure, bromination to obtain the target product 5, the s...

Claims

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Application Information

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IPC IPC(8): C07D263/34
CPCC07D263/34C07C45/64C07C269/00C07D263/38C07C271/12C07C49/84
Inventor 李书耘陈芳军
Owner 湖南华腾制药有限公司