Reaction #1833282

Reaction equation

4-chloro-2-hydroxybenzoic acid

borane

→

title compound

Yield 82.1%

5-Chloro-2-(hydroxymethyl)phenol

Yield 82.1%

Solvents

THF

THF

Conditions

Workup

1. 1
   TemperatureThe mixture was refluxed at 80° C. for 2.5 h
2. 2
   OtherThe solvent was removed in vacuo
3. 3
   Otherpurified on silica (100 g)
4. 4
   Otherevaporated in vacuo

Procedure

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.

Source