HCID 22049841, compound → HCID 22049843, compound

Participants

Reaction Steps

To a solution of 1-[bis-(4-chloro-phenyl)-methanesulfonyl]-propan-2-one (Example 1, 0.63 g, 1.7 mmol) in a mixture of 10 mL of acetic acid and 60 mL of dichloromethane was added pyridine hydrobromide perbromide (0.62 g, 1.9 mmol) using a procedure such as those described in Grossert J. S. et al., Can. J. Chem. 1984; 62:798. The reaction mixture was stirred at room temperature for 18 hours and then evaporated to give an oil. The oil was dissolved in 200 mL of ethyl acetate, washed with three 50 mL portions of 5% aqueous sodium bicarbonate and then with 50 mL of brine. The organic layer was separated, dried (sodium sulfate), filtered, and then evaporated to afford an oil, which was chromatographed (silica gel, eluting with 30% ethyl acetate in hexane) to give 0.37 g (48%) of a white solid with mp 122–123° C.; 1H NMR (deuterochloroform): δ 4.03 (s, 2H), 4.09 (s, 2H), 5.64 (s, 1H), 7.33–7.41 (m, 4H), 7.51–7.58 (m, 4H); ms: m/z 435 (m−1) APCI-.

Provenance & Evidence