Boron tribromide → 4-(4-Hydroxybutyl)phenol

Participants

Reaction Steps

To a stirred solution of 4-(4-methoxyphenyl)butanol (1 equiv.) in dry dichloromethane at −10° C. under an argon atmosphere was added boron tribromide (2.7 equiv., using a 1 M solution of boron tribromide in CH2Cl2). Stirring was continued at that temperature until completion of the reaction (4 hours). Unreacted boron tribromide was destroyed by addition of aqueous saturated NaHCO3 solution at 0° C. The resulting mixture diluted with CH2Cl2 and water, the organic phase was separated, washed with brine, dried (MgSO4) and evaporated. Purification by flash column chromatography on silica gel (30% diethyl ether-hexane) afforded the title compound in 42% yield.

Provenance & Evidence