Borane → 4-Chloro-3-(hydroxymethyl)phenol

Participants

Reaction Steps

To a solution of 2-chloro-5-hydroxybenzoic acid (2.96 g, 17.2 mmol, Apin) in THF (60 ml) under nitrogen was slowly added 1 M borane in THF (30 ml, 30.0 mmol). The suspension was stirred for 20 minutes at ambient temperature. The mixture was refluxed at 80° C., under nitrogen for 3 h. The reaction mixture was allowed to cool to ambient temperature then carefully quenched using methanol (20 ml). The mixture was then refluxed for a further 1 h at 80° C. under nitrogen. The solvent was removed in vacuo and left under high pressure vacuum overnight to give the title compound as a cloudy gum (3.38 g); LCMS: (System 4) (M-H)−=157, tRET=1.50 min.

Provenance & Evidence