(Dimethyl sulfide)trihydroboron → (1-(4-Bromophenyl)cyclopropyl)methanol

Participants

Reaction Steps

To a solution of 1-(4-bromophenyl)cyclopropane carboxylic acid (3.0 g, 12.4 mmol) in dry THF (40 mL) under nitrogen atmosphere, was added borane dimethyl sulphide (8.83 mL, 19.8 mmol, 2 M solution in DCM) at 0° C. The reaction mixture was stirred at r.t for 4 h. After the completion of reaction as confirmed by TLC, the reaction mixture was quenched by dropwise addition of methanol until effervescence stopped. Volatiles were evaporated in vacuo and the compound was diluted with ethyl acetate (80 mL). The organic layer was separated; washed with water (3×10 mL), dried over Na2SO4 and concentrated. The crude product obtained was purified by column chromatography (silica gel, 1:4 EtOAc:Pet Ether) to afford title compound (2.7 g, 96%) as a solid.

Provenance & Evidence