Trimethylsulfonium iodide → 2-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

Participants

Reaction Steps

Potassium tert-butoxide (18.48 g, 165.0 mmol) was added to a rapidly stirred suspension of 4-chloro-4′-iodobenzophenone (51.38 g, 150.0 mmol) and trimethylsulphonium iodide (33.66 g, 165.0 mmol) in dimethylsulphoxide (200 ml) and the resulting mixture was stirred at room temperature for 3 hours. The mixture was diluted with ethyl acetate (500 ml), washed with water (3×500 ml) and then with brine (500 ml). The organic layer was separated and the solvent removed in vacuo to afford (RS)-2-(4-chlorophenyl)-2-(4-iodophenyl)oxirane (53.48 g, 100%) as a pale yellow oil that solidified upon standing to afford an off-white solid. 1H NMR (DMSO-d6) 7.76 (2H, d), 7.45 (2H, d), 7.34 (2H, d), 7.12 (2H, d), 3.32 (2H, m). MS: [M−H]− 355.

Provenance & Evidence