Synthesis
4-Iodotoluene (Compound 1C, 25 g) was added with N-bromosuccinimide (23.5 g) and benzoyl peroxide (375 mg) in carbon tetrachloride (375 ml) and heated to reflux for 7 hours under light conditions. After completion of the reaction, the mixture was stirred at room temperature overnight. Subsequently, the insoluble material was removed by filtration and the filtrate was concentrated under reduced pressure. The concentrated residue was recrystallized with ethyl acetate and hexane to afford the target product 4-iodobenzyl bromide (Compound 1D) in 60.3% yield.
[0027] NMR hydrogen spectral data (CDCl3, with TMS as internal standard): δ 7.72 (d, 2H), 7.14 (d, 2H), 4.39 (s, 2H).
References
[1] Macromolecules, 2013, vol. 46, # 12, p. 4754 - 4763
[2] Acta Crystallographica Section C: Crystal Structure Communications, 2003, vol. 59, # 4, p. o216-o218
[3] Journal of Materials Chemistry C, 2015, vol. 3, # 4, p. 734 - 741
[4] Chemistry - An Asian Journal, 2017, vol. 12, # 6, p. 690 - 697
[5] Journal of Organic Chemistry, 2014, vol. 79, # 1, p. 223 - 229
