(Dimethyl sulfide)trihydroboron → 2-(3-(Bromomethyl)-5-chlorophenyl)ethanol

Participants

Reaction Steps

A solution of borane dimethyl sulfide complex (2M in THF, 2.8 mL) was added portionwise over 5 minutes to a solution of 2-(3-(bromomethyl)-5-chlorophenyl)acetic acid [Aromatic Intermediate 8, step a] (0.73 g) in dry THF (10 mL) at room temperature. The resulting effervescing solution was stirred for 1 hour, then cooled in ice-water and quenched by the portionwise addition of methanol (3 mL) over 5 minutes. The solution was stirred at room temperature for a further 20 minutes and then concentrated in vacuo. The residue was purified by flash chromatography on silica eluted with 25% ethyl acetate in isohexane to afford the crude subtitled compound as a white solid. Yield 0.46 g.

Provenance & Evidence