Synthesis
Example 15 Synthesis of 2-phenylethanesulfonyl chloride: N-chlorosuccinimide (534 mg, 4.00 mmol) was dissolved in a 2M HCl-CH3CN mixed solvent (267.4 μL - 1.34 mL, 3v/w volume relative to N-chlorosuccinimide). To this solution, a CH3CN solution (267.4 μL, 0.5 v/w relative to the volume of N-chlorosuccinimide) of 2-phenylethanethiol (134 μL, 1.00 mmol) was slowly added at 10 °C. After 30 min of reaction, ether was added to the reaction mixture, followed by three extractions with brine. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 2-phenylethanesulfonyl chloride (195.5 mg, 95.4% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 7.43-7.27 (m, 5H), 3.98-3.92 (m, 3H), 3.41-3.35 (m, 1H).
References
[1] Bioorganic and Medicinal Chemistry Letters, 2002, vol. 12, # 8, p. 1181 - 1184
[2] Patent: US2015/329533, 2015, A1. Location in patent: Paragraph 0147; 0148
[3] Advanced Synthesis and Catalysis, 2015, vol. 357, # 18, p. 3825 - 3830
[4] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3183 - 3203
[5] Journal of the American Chemical Society, 1991, vol. 113, # 6, p. 2259 - 2263
