3-Phenylbenzenesulfonyl chloride

Synthesis

[1,1'-Biphenyl]-3-yl(benzyl)thiolane (450 mg, 1.63 mmol) was used as a raw material to synthesize [1,1'-biphenyl]-3-sulfonyl chloride according to General Method J. The synthesis was carried out by using a mixture of acetic acid/water (3:1, v/v; 0.1 mmol/mL) and N-chlorobutanediyl chloride (3:1, v/v; 0.1 mmol/mL). The procedure was as follows: the raw material was dissolved in a mixed solvent of acetic acid/water (3:1, v/v; 0.1 mmol/mL) at room temperature, and N-chlorosuccinimide (NCS, 6 equiv) was added. The reaction mixture was stirred at the same temperature for 3-6 h. The reaction progress was monitored by HPLC. After completion of the reaction, the solvent was removed by concentration under reduced pressure, saturated aqueous sodium bicarbonate was added and extracted with ethyl acetate (EtOAc). The organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the crude product was concentrated under reduced pressure and purified by Combifiash silica gel column chromatography (100% hexane as eluent) to afford [1,1'-biphenyl]-3-sulfonyl chloride 250 mg (5.9% yield) as a colorless solid. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 8.28-8.24 (m, 1H), 8.05-8.01 (m, 1H), 7.98-7.95 (m, 1H), 7.74-7.68 (m, 1H), 7.66-7.61 (m, 2H), 7.56-7.49 (m, 2H), 7.49- 7.43 (m, 1H).

References

[1] ChemMedChem, 2016, vol. 11, # 23, p. 2607 - 2620
[2] Patent: WO2018/52903, 2018, A1. Location in patent: Page/Page column 22-23; 58