p-Bromobenzenesulfonyl chloride → (S)-(-)-3-Chloro-1-phenyl-1-propanol

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-1-phenyl-1,3-propanediol (125 g, 0.822 mole) in methyl tert-butyl ether (500 mL) was added triethylamine (135 mL). The reaction mixture was cooled to 0° C. and a solution of 4-bromobenzenesulfonyl chloride (230 g, 0.92 mole) in methyl tert-butyl ether (300 mL) and tetrahydrofuran (300 mL) was added dropwise over 3 hour. After the addition, the reaction mixture was stirred at 0° C. for three hours and was then warmed to ambient temperature. After stirring at ambient temperature for 18 hours, benzyltriethylammonium chloride (210 g, 0.92 mole) was added and the resulting mixture was heated at 55° C. for three hours. The reaction mixture was cooled to ambient temperature and then diluted with water. After separation of the organic phase, the aqueous phase was extracted two times with diethyl ether. The combined organic extracts were washed with 1.0 N hydrochloric acid, saturated aqueous sodium bicarbonate, water, saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure to provide an off-white solid (160 g). This solid was subjected to silica gel chromatography, eluting with ethyl acetate/hexane (1:9) to provide 110 grams (80%) of the title compound.

Provenance & Evidence