2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethyl methanesulfonate

Uses

2-[2-(2,2,2-Trifluoroethoxy)phenoxy]ethyl Methanesulfonate is an intermediate of Silodosin (S465000) which is an α1a-adrenoceptor antagonist and used in the treatment of benign prostatic hypertophy.

Synthesis

Anhydrous AlCl3 ( 165 g, 1 .24 mol) and 200 mL of anhydrous dichloromethane were mixed, cooled to -5 under nitrogen protection, methane sulfonyl chloride was added dropwise with stirring, and then stirred at room temperature for 30 min after the dropwise addition, a solution of 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethanol ( 100 g, 0.62 mol) in dichloromethane ( 70 mL) was added dropwise with stirring at room temperature after the dropwise addition, and the internal temperature was not more than 5 . The internal temperature was not more than 5 , and the reaction progress was detected by thin-layer chromatography after the dropwise addition and stirring at room temperature for 30 h. The reaction solution was slowly poured into 800 mL of ice water with stirring, and the organic layer was separated, the aqueous layer was extracted with dichloromethane (6 120 mL), and the organic layers were combined, washed with saturated brine, saturated sodium bicarbonate solution and dried with anhydrous sodium sulfate, and then filtered, and the filtrate was concentrated. Ethyl acetate. The target compound 2-[2-(2,2,2-trifluoroethoxy)phenoxy]ethyl methanesulfonate.