Synthesis
General procedure for the synthesis of 4-bromomethylbiphenyl from 4-biphenylmethanol: Carbon tetrabromide (8.99 g, 27.1 mmol) and triphenylphosphine (7.11 g, 27.1 mmol) were sequentially added to a solution of dichloromethane (100 mL) containing biphenyl-4-ylmethanol (5.00 g, 27.1 mmol) at room temperature with continuous stirring. The reaction mixture was stirred at room temperature for 1.5 h before the solvent was removed by distillation under reduced pressure. The resulting crude product was purified by silica gel column chromatography with an eluent ratio of 1:20 ether/cyclohexane, resulting in 4-bromomethylbiphenyl (6.37 g, 95% yield) as a white solid.1H NMR (400 MHz, CDCl3) data were as follows: δ 7.60 (4H), 7.45 (4H), 7.35 (1H), 4.55 (2H).
References
[1] Organic Letters, 2013, vol. 15, # 9, p. 2210 - 2213
[2] Patent: WO2005/26120, 2005, A1. Location in patent: Page/Page column 21
[3] Patent: WO2004/110974, 2004, A1. Location in patent: Page 22
[4] Organic Letters, 2012, vol. 14, # 21, p. 5428 - 5431,4
[5] Organic Letters, 2018, vol. 20, # 10, p. 3061 - 3064
