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

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.

1. temperatureThe mixture was refluxed at 80° C., under nitrogen for 3 h
2. temperatureto cool to ambient temperature
3. customthen carefully quenched
4. temperatureThe mixture was then refluxed for a further 1 h at 80° C. under nitrogen
5. customThe solvent was removed in vacuo
6. waitleft under high pressure vacuum overnight

ORD record

ord-5a78403f7b9b4bdda3703799645b9c73

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2