Synthesis
General procedure for the synthesis of 4-bromomethylbenzenesulfonyl chloride from p-toluenesulfonyl chloride: to a stirred solution of p-toluenesulfonyl chloride (20 g, 104.9 mmol) in carbon tetrachloride (500 mL) was added sequentially N-bromosuccinimide (20.6 g, 115.7 mmol) and benzoyl peroxide (2.54 g, 10.84 mmol) at room temperature. The reaction mixture was refluxed for 10 hours and then filtered through a diatomaceous earth pad. The filtrate was concentrated under reduced pressure to give a yellow oil. The oily substance was recrystallized using hexane as eluent to give 4-bromomethylbenzenesulfonyl chloride (20.6 g, 65% yield) as a final white solid.
References
[1] Bulletin of the Korean Chemical Society, 2013, vol. 34, # 5, p. 1487 - 1493
[2] Advanced Synthesis and Catalysis, 2018, vol. 360, # 21, p. 4197 - 4204
[3] Journal of the American Chemical Society, 1957, vol. 79, p. 4232
[4] Journal of Medicinal Chemistry, 1990, vol. 33, # 9, p. 2437 - 2451
[5] Patent: US5318980, 1994, A
