Dimethyl Sulfide → (4-Bromo-2-methylphenyl)methanol

Participants

Reaction Conditions

Reaction Steps

Borane-dimethyl sulfide complexe (2.5 eq.) was added to a stirred solution of commercially available 4-bromo-2-methylbenzoic acid (1 eq.) in THF (0.3M). The mixture was reflux for 3 h. at without a condensor allowing the SMe2 to escape. The final reaction concentration was 0.5M. The mixture was cooled to 0° C. and quenched with a slow addition of HCl 1N. The resulting mixture was extracted with Et2O. The organic extract was washed with water, brine, dried over MgSO4 filtered and concentrated to afford the desired material as a yellow solid.

Provenance & Evidence