Synthesis
General procedure for the synthesis of 1-(1-bromoethyl)-4-fluorobenzene from 1-(4-fluorophenyl)-1-ethanol: 1-(4-fluorophenyl)ethanol (0.455 mL, 3.57 mmol) was mixed with phosphorus tribromide (0.673 mL, 7.13 mmol) in chloroform (10 mL) and heated to a temperature of 70°C for 3 days. Upon completion of the reaction, the reaction mixture was quenched by pouring it into ice water and diluted with ethyl acetate. The organic layer was separated, washed sequentially with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuum to obtain the crude product. The crude product was purified by silica gel column chromatography with hexane/dichloromethane (2:1) as eluent to afford 1-(1-bromoethyl)-4-fluorobenzene (154 mg, 0.758 mmol, 21.3% yield) as a colorless oil.1H NMR (400 MHz, CDCl3) δ 7.49-7.40 (m, 2H), 7.09-7.00 (m , 2H), 5.23 (q, J = 7.0 Hz, 1H), 2.06 (d, J = 6.8 Hz, 3H).
References
[1] Journal of the American Chemical Society, 2016, vol. 138, # 34, p. 10774 - 10777
[2] Patent: US2012/46301, 2012, A1. Location in patent: Page/Page column 30; 31
[3] Patent: WO2018/148626, 2018, A1. Location in patent: Page/Page column 152
[4] Tetrahedron, 1977, vol. 33, p. 1581 - 1585
[5] Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical & Analytical, 1984, vol. 23, # 1, p. 60 - 62
