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Preparation method of substituted phenyl methyl ether

A technology of phenyl methyl ether and dimethyl formamide, which is applied in the field of preparation of 2-phenyl methyl ether, can solve the problems of large environmental pollution, unsuitable for industrialized production, complicated purification process and the like, and achieves high safety, Good product quality and simple post-processing effect

Active Publication Date: 2013-10-16
YANGTZE RIVER PHARM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is following shortcoming in this method: 1. adopted the raw material that contains iodine atom, cause aftertreatment to pollute environment bigger; 2. the yield of reaction is 71%; 3. purification process is complicated, is not suitable for suitability for suitability for industrialized production

Method used

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  • Preparation method of substituted phenyl methyl ether
  • Preparation method of substituted phenyl methyl ether

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Experimental program
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Effect test

Embodiment 1

[0024]

[0025] In the there-necked flask equipped with mechanical stirring and reflux condenser, add 2-methoxyphenol (10g, 81mmol), dimethylformamide (100ml) and potassium carbonate (12.4g, 90mmol), stir, add 2, 2,2-Trifluoroethyl methanesulfonate (16g, 89mmol), stirred, heated to 150°C, maintained at reflux for 2 hours, stopped the reaction, filtered with suction, washed with dimethylformamide, combined the filtrates, concentrated under reduced pressure to dry (HPLC purity 96.8%), the residue was extracted three times with ether, the extracts were combined, washed twice with 10% sodium hydroxide, washed with water until neutral, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated to dryness under reduced pressure to obtain 14.3 g of the product, with a yield of 86% (HPLC purity: 99.68%).

[0026] 1 H NMR (CDCl 3 ): 7.060~6.895, m, ArH; 4.418~4.355, t, CH 2 ;3.872,s,CH 3 .

Embodiment 2

[0028]

[0029] In the there-necked flask equipped with mechanical stirring and reflux condenser, add 2-methoxyphenol (10g, 81mmol), dimethylformamide (100ml) and sodium hydroxide (3.6g, 90mmol), stir, add 2 , 2,2-trifluoroethyl methanesulfonate (16g, 89mmol), stirred, heated to 100°C, maintained at reflux for 6 hours, stopped the reaction, filtered with suction, washed with dimethylformamide, combined the filtrates, concentrated under reduced pressure To dryness (HPLC purity 96.7%), the residue was extracted three times with ether, the combined extracts were washed twice with 10% sodium hydroxide, washed with water until neutral, and dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated to dryness under reduced pressure to obtain 15.2 g of the product, with a yield of 91.5% (HPLC purity: 99.70%).

[0030] Elemental analysis (C 9 h 9 f 3 o 2 ): theoretical value (%) is C52.43, H 4.40, F27.65, O 15.52; experimental value (...

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Abstract

The invention discloses a preparation method of 2-(2,2,2-trifluoroethoxy)phenyl methyl ether. The method adopts 2-metoxyphenol as the starting material and takes 2,2,2-trifluoroethyl methanesulfonate as the substituent group for substitution reaction under the alkaline environment. The preparation method has the advantages that the yield is high, and the used raw materials are cheap and available; the leaving group of chlorine atoms, bromine atoms and iodine atoms can be avoided, thereby reducing pollution; and the process is easy to control, the operation and aftertreatment are simple, the safety is high, the product quality is good, and the cost is low, thereby being more suitable for industrial production.

Description

technical field [0001] The present invention relates to the synthesis of pharmaceutical compounds, more specifically, to a preparation method of 2-(2,2,2-trifluoroethoxy)phenylmethyl ether. Background technique [0002] Silodosin is selective alpha 1A Blocking drugs for the treatment of benign prostatic hypertrophy with urinary disorders. The product was jointly developed by Japan's Kissei and Daiichi Pharmaceutical Company, and has been launched in Japan and the United States. [0003] 2-(2,2,2-trifluoroethoxy)phenylmethyl ether, which is an important intermediate in the synthesis of silodosin. Jusheng Pharmaceutical Industry Co., Ltd. disclosed a method for preparing silodosin in Chinese patent CN101048376A published on October 3, 2007, and disclosed that silodosin was synthesized with its derivative - phenoxyethane compound pungent. [0004] Tangerine Pharmaceutical Industry Co., Ltd. described a preparation method of 2-(2,2,2-trifluoroethoxy) phenyl methyl ether in U...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/225C07C41/16
Inventor 孙田江陆宏国孟霆查大俊江东葵张海波陈言德金荣庆李冬梅王志贤尹必喜
Owner YANGTZE RIVER PHARM GRP CO LTD
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