Synthesis
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.
References
[1] Journal of Medicinal Chemistry, 2013, vol. 56, # 21, p. 8432 - 8454
[2] Synlett, 2014, vol. 25, # 1, p. 123 - 127
[3] Journal of Organic Chemistry, 1985, vol. 50, # 2, p. 283 - 284
[4] Patent: US2003/195259, 2003, A1
[5] Patent: WO2006/101977, 2006, A2. Location in patent: Page/Page column 112
