Synthesis
General procedure for the synthesis of 1-(1-bromoethyl)-4-nitrobenzene from 1-(4-nitrophenyl)ethanol: A mixture of 1-(4-nitrophenyl)ethanol (10.0 g, 66 mmol), N-bromosuccinimide (11.8 g, 66 mmol) and benzoyl peroxide (160 mg, 0.66 mmol) in carbon tetrachloride (100 mL) was The solution was heated to reflux and the reaction was continued for 1.5 hours. Upon completion of the reaction, the reaction mixture was cooled to 0 °C and filtered through a sintered funnel. The solid obtained by separation was washed once with hexane (50 mL), and the filtrate was combined and concentrated. Finally, the target product 1-(1-bromoethyl)-4-nitrobenzene (7.52 g, 49% yield) was purified by column chromatography (2-5% ethyl acetate/hexane as eluent). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts of δ 8.21 (d, 2H), 7.58 (d, 2H), 5.22 (q, 1H), 2.05 (d, 3H).
References
[1] Patent: WO2008/23235, 2008, A1. Location in patent: Page/Page column 57
[2] Journal of the American Chemical Society, 1968, vol. 90, # 2, p. 418 - 426
[3] Journal of Organic Chemistry, 1969, vol. 34, p. 1086 - 1089
[4] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1987, vol. 26, p. 68 - 70
[5] Journal of the American Chemical Society, 1983, vol. 105, # 3, p. 320 - 324
