Synthesis
A THF solution (50 mL) of 3-(3-bromophenyl)propionic acid (5 g, 21.83 mmol, 1.00 eq.) was added to a 250 mL three-necked round-bottomed flask under nitrogen protection. The reaction system was cooled to 0 °C and the borane tetrahydrofuran complex solution (1 mol/L, 75 mL, 74.22 mmol, 3.40 eq.) was slowly added dropwise with stirring. After the dropwise addition, the reaction mixture was gradually warmed to room temperature and stirred overnight. After completion of the reaction, the mixture was slowly poured into 150 mL of 1 mol/L HCl solution and extracted with dichloromethane (3 x 200 mL). The organic phases were combined, washed with 300 mL of saturated saline, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography with dichloromethane/methanol (10:1, v/v) as eluent. The target fraction was collected and concentrated under reduced pressure to afford 3-(3-bromophenyl)propan-1-ol (1.3 g, 28% yield) as a colorless oil.1H NMR (DMSO-d6, 400 MHz) δ: 7.41-7.20 (m, 4H), 4.51-4.48 (t, 1H), 3.41-3.34 (m, 2H), 2.67-2.59 (m, 2H), 1.73-1.73 (m, 2H). 2H), 1.73-1.66 (m, 2H).
References
[1] Patent: US2004/10019, 2004, A1. Location in patent: Page 160; 167
[2] Patent: WO2006/101977, 2006, A2. Location in patent: Page/Page column 56
[3] Journal of Organic Chemistry, 2010, vol. 75, # 15, p. 5178 - 5194
[4] Angewandte Chemie - International Edition, 2018, vol. 57, # 15, p. 4058 - 4062
[5] Angew. Chem., 2018, vol. 130, p. 4122 - 4126,5
