68120-35-4

7697-26-9

68120-35-4

GENERAL METHODS: 3-Bromo-4-methylbenzoic acid (20.70 g, 81.82 mmol) was dissolved in tetrahydrofuran (THF, 250 mL) and the solution was cooled to 0°C. Borane-THF complex (1.0 M in THF, 164 mL) was slowly added under stirring. The reaction mixture was gradually warmed to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium carbonate solution (Na2CO3, 100 mL). Subsequently, the reaction mixture was extracted with ethyl acetate (EtOAc, 3 x 100 mL). The organic layers were combined, dried with anhydrous magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure to give the crude product as a colorless liquid. The crude product was further purified by distillation under reduced pressure (0.8 mbar) and the fractions distilled at 90 °C were collected to give 3-bromo-4-methylbenzyl alcohol (16.30 g, 99%) as a colorless liquid.