Synthesis
General procedure for the synthesis of 1-bromo-4-(3-bromopropyl)benzene from 4-bromobenzenepropanol: To a solution of 4-bromobenzenepropanol (4.0 g, 19 mmol) in THF (30 mL) was added triphenylphosphine (PPh3, 6.3 g, 24 mmol) and carbon tetrabromide (CBr4, 8.0 g, 24 mmol) in turn at 0 °C and under argon protection. The reaction mixture was stirred at 0 °C for 15 min, then raised to room temperature and continued stirring for 15 h. The reaction was carried out under reduced pressure by distillation. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the resulting crude product was purified by silica gel column chromatography (eluent: hexane) to afford 1-bromo-4-(3-bromopropyl)benzene as a colorless oil (3.5 g, 66% yield).The 1H NMR (500 MHz, DMSO-d6) data were as follows: δ 2.03-2.12 (m, 2H), 2.68 (t, J=7.5 Hz. 2H), 3.49 (t, J=6.5 Hz, 2H), 7.19 (d, J=8.3 Hz, 2H), 7.47 (d, J=8.3 Hz, 2H).
References
[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 6, p. 1546 - 1559
[2] Patent: WO2006/101977, 2006, A2. Location in patent: Page/Page column 114
[3] Patent: WO2008/8234, 2008, A1. Location in patent: Page/Page column 110
[4] Organic Letters, 2010, vol. 12, # 24, p. 5783 - 5785
[5] Tetrahedron, 1990, vol. 46, # 20, p. 7247 - 7262
