Synthesis
General procedure for the synthesis of 2-bromophenylpropanol from 3-(2-bromophenyl)propionic acid: to an anhydrous tetrahydrofuran (5.0 mL) solution of 3-(2-bromophenyl)propionic acid (1.0 g, 4.4 mmol) was slowly added a tetrahydrofuran solution of the borane-tetrahydrofuran complex (1.0 M, 7.0 mL, 7.0 mmol) at 0 °C, and the addition time was controlled at 15 The addition time was controlled to be more than 15 minutes. After addition, the reaction mixture was continued to be stirred at 0 °C for 1 hour. Upon completion of the reaction, the residual borane was quenched by careful addition of water (1 mL) and the solvent was subsequently removed under reduced pressure. The resulting residue was dissolved in ether (20 mL), the organic layer was washed sequentially with water (20 mL) and brine (20 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure to afford 3-(2-bromophenyl)propan-1-ol as a colorless oil (938 mg, quantitative yield). The product did not require further purification and could be used directly in the subsequent reaction.
References
[1] Patent: US2016/95858, 2016, A1. Location in patent: Paragraph 4462; 4463
[2] Journal of Organic Chemistry, 1989, vol. 54, # 23, p. 5574 - 5580
[3] Patent: WO2010/45212, 2010, A2. Location in patent: Page/Page column 222-223
[4] Patent: US2013/184313, 2013, A1. Location in patent: Paragraph 1274; 1275
[5] Angewandte Chemie - International Edition, 2018, vol. 57, # 18, p. 5124 - 5128
