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

To a solution of 4-chloro-2-hydroxybenzoic acid (2.0 g, 11.6 mmol, Aldrich) 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 as a white solid (1.51 g);

1. temperatureThe mixture was refluxed at 80° C. for 2.5 h
2. customThe solvent was removed in vacuo
3. custompurified on silica 100 g
4. customevaporated in vacuo

ORD record

ord-cc80d2f4ce7e4809b35c449c205e8585

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2