Borane → 5-Chloro-2-(hydroxymethyl)phenol

Participants

Reaction Steps

To a solution of 4-chloro-2-hydroxybenzoic acid (Aldrich; 2.0 g, 11.6 mmol) in THF (50 ml) was added dropwise 1 M borane in THF (20.9 ml, 20.9 mmol). The suspension was allowed to stir for 30 min at ambient temperature. The mixture was refluxed at 80° C. for 2.5 h. The solvent was removed in vacuo. The residue was loaded in dichloromethane and purified on silica (100 g) using 0-100% ethyl acetate/cyclohexane. The appropriate fractions were combined and evaporated in vacuo to give the title compound (1.51 g) as a white solid; LCMS (System 1): (M-H)−=157, tRET=2.44 min.

Provenance & Evidence