HCID 67078824, compound → HCID 89581362, compound

Participants

Reaction Steps

To a solution of 2-(4-bromophenyl)-2-phenoxyacetic acid (6 g, 19.6 mmol) in anhydrous tetrahydrofuran (100 mL) was added borane-tetrahydrofuran complex (1 M, 40 mL) at −5° C. The solution was stirred at room temperature for 15 hours. After 2 hours, LC-MS showed the desired product was obtained. Water:acetic acid (1:1, 50 mL) was added at 0° C. to quench the reaction, the mixture was added 10 mL saturated sodium bicarbonate to adjust pH=7, extracted with ethyl acetate (100 mL). Then combined and concentrated the organic layers. The crude product was purified by column chromatography (silica gel, dichloromethane/menthol=40:1) to give 2-(4-bromophenyl)-2-phenoxyethanol (5 g, 80%). LCMS (M+H+) m/z: calcd 292.06. found 292.

Provenance & Evidence