2-Chloro-6-hydroxybenzoic acid → 3-Chloro-2-(hydroxymethyl)phenol

To a solution of 2-chloro-6-hydroxybenzoic acid (for a preparation see Intermediate 5)(1.45 g, 8.39 mmol) in THF (20 ml) at ambient temperature under nitrogen was added 1 M borane-tetrahydrofuran complex (16 ml, 16.0 mmol, Aldrich). The solution was stirred at ambient temperature for 10-15 min and then heated to 80° C. for 1 h. The resulting suspension was allowed to cool to ambient temperature and quenched with methanol (10 ml). The resulting solution was heated to 80° C. for 30 min and at ambient temperature overnight. The solvent was removed in vacuo and the oil dried under high vacuum to give the title compound as a solid (1.36 g); LCMS: (System 1) (M-H)−=157, tRET=2.22 min.

1. customat ambient temperature
2. additionwas added 1 M borane-tetrahydrofuran complex (16 ml, 16.0 mmol, Aldrich)
3. temperatureheated to 80° C. for 1 h
4. temperatureto cool to ambient temperature
5. customquenched with methanol (10 ml)
6. temperatureThe resulting solution was heated to 80° C. for 30 min and at ambient temperature overnight
7. customThe solvent was removed in vacuo
8. customthe oil dried under high vacuum

ORD record

ord-4d39c51428c44c04bdf0bf81ba307e68

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399436B2