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Method for preparing 2-(2,2,2-trifluoroethoxy)phenol

A technology of trifluoroethoxy and trifluoroethanol, applied in 2-(2, can solve the problems of harsh reaction conditions, easy decomposition, strong corrosion, etc., and achieve the effect of being suitable for industrial production, optimizing reaction conditions, and simplifying reaction operations

Inactive Publication Date: 2007-05-16
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] 1) Reaction a requires an extremely expensive and imported reagent 2,2,2-trifluoroiodoethane, which is unstable in nature, easy to decompose, difficult to store and transport, and requires anhydrous reaction conditions, which is not suitable for production;
[0007] 2) Reaction step b also requires expensive reagent boron tribromide, boron tribromide is unstable, decomposes rapidly when exposed to light, water, and air, and is highly corrosive and irritating. The reaction conditions are extremely harsh and difficult for industrial production

Method used

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  • Method for preparing 2-(2,2,2-trifluoroethoxy)phenol

Examples

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Embodiment 1

[0016] Embodiment 1, the preparation of 2-(2,2,2-trifluoroethoxy) nitrobenzene (III):

[0017] Add o-nitrochlorobenzene (II) 100g, 50% sodium hydroxide 260g, phase transfer catalyst tetrabutylammonium bromide 8g in the reaction bottle, stir, heat up to 60 ° C, drop 2,2,2-trifluoroethanol 68g, dropwise, stirred and reacted at 70°C for 6 hours, cooled, filtered with suction, washed with water, and dried to obtain 124g of orange-red solid (III), mp 53-5°C, yield 88.4%.

[0018] 1 HNMR (CDCL 3 )δ: 4.50 (q, 2H, -CH 2 CF 3 ), 7.13-7.90 (m, 4H, Ar-H)

Embodiment 2

[0019] The preparation of embodiment 2,2-(2,2,2-trifluoroethoxy)aniline (IV):

[0020] Add 120 g of 2-(2,2,2-trifluoroethoxy) nitrobenzene (III), 1.5 L of absolute ethanol, and 10 g of 10% palladium carbon into the hydrogenation kettle, hydrogenate at normal pressure, stir the reaction at room temperature for 12 hours, pump After filtration, the filtrate was concentrated under reduced pressure to obtain 95 g of light yellow solid (IV), mp58-60°C, yield 91.6%.

[0021] 1 HNMR (CDCL 3 )δ: 3.84 (brs, 2H, -NH 2 ), 4.42 (q, 2H, -CH 2 CF 3 ), 6.70-7.26 (m, 4H, Ar-H)

Embodiment 3

[0022] The preparation of embodiment 3,2-(2,2,2-trifluoroethoxy)phenol (I):

[0023] Add 20% (W / W) sulfuric acid 210g in the reaction flask, cool in an ice-water bath, stir, add 2-(2,2,2-trifluoroethoxy)aniline (IV) 80g, react for 30 minutes, add dropwise A solution made of 30g of sodium nitrate and 50g of water, after dripping, reacted at 0-5°C for 2 hours, then frozen for later use.

[0024] Add 200g of 20% (W / W) sulfuric acid, 100g of sodium sulfate, and 500ml of toluene into the reaction flask, stir, heat to 70°C, add the above-mentioned diazonium salt solution dropwise, and continue the reaction for 2 hours, cool, and separate the liquids. Extract the aqueous phase with 200ml×2 toluene, combine the toluene layers, wash with water, concentrate to 1 / 3 volume, extract with 30% (W / W) sodium hydroxide 200g×3, combine the aqueous layers, acidify with 2N hydrochloric acid, and add 200ml×2 toluene Extract and combine the toluene layers, dry over anhydrous sodium sulfate, filter,...

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Abstract

The invention discloses a preparing method of 2-(2,2,2-trifluoro ethoxy) phenol (I) (the structural formula as follows), which comprises the following steps: adopting o-nitrochlorobenzene as raw material; etherifying 2,2,2-trifluoro ethoxy; reducing through hydrogen; diazotizing; proceeding hydroxy decomposition to obtain the product.

Description

technical field [0001] Process for the preparation of 2-(2,2,2-trifluoroethoxy)phenol. Background technique [0002] The structural formula of Silodosin (KMD-3213, KAD-3213) is as follows, and it is jointly developed by Japanese Kissei and Daiichi companies α 1 - Adrenergic receptor antagonists, clinically used in the treatment of benign prostatic hyperplasia. This product was first listed in Japan in 2006, and there is no synthesis literature report in China at present. 2-(2,2,2-trifluoroethoxy)phenol is an important intermediate in the synthesis of Silodosin (structural formula below). Its synthetic method has only the synthetic route reported in the Japanese Kissei (jusheng) company patent (EP600675), and its route is as follows: [0003] [0004] [0005] The disadvantages of this route are: [0006] 1) Reaction a requires an extremely expensive and imported reagent 2,2,2-trifluoroiodoethane, which is unstable in nature, easy to decompose, difficult to store an...

Claims

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Application Information

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IPC IPC(8): C07C201/12C07C205/37
Inventor 陈国华罗小川李强王先登黄文龙
Owner CHINA PHARM UNIV
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