3-Bromo-2-methylbenzoic Acid → (3-Bromo-2-methylphenyl)methanol

To a solution of 3-bromo-2-methyl benzoic acid (35 g, 160 mmol) in THF (200 mL) was added borane THF complex (1.0 M, 210 mL, 210 mmol). The mixture was allowed to stir for 24 hours. The reaction was quenched with water. The solvent THF was removed under reduced pressure. The resulting solid was dissolved in ethyl acetate (500 mL), washed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine. The combined organic layers were dried over sodium sulfate and concentrated to afford (3-bromo-2-methylphenyl)methanol.

1. customThe reaction was quenched with water
2. customThe solvent THF was removed under reduced pressure
3. dissolutionThe resulting solid was dissolved in ethyl acetate (500 mL)
4. washwashed with 1N hydrochloric acid, saturated sodium bicarbonate, and brine
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated

ORD record

ord-f78fa7cad65f4569865267fde3203bcf

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09108947B2