Dimethyl Sulfoxide → 2-(4-Chlorophenyl)-2-(4-iodophenyl)oxirane

Participants

Reaction Steps

Sodium hydride (60% dispersion in oil, 128 mg, 3.2 mmol) was placed under N2 then DMSO (5 mL) was added. Trimethylsulfonium iodide (0.66 g, 3.2 mmol) was added as a solid after 15 minutes, followed after a further 30 minutes by (4-chloro-phenyl)-(4-iodo-phenyl)-methanone (1 g, 2.9 mmol). The mixture was stirred at room temperature for 24 hours then diluted with ethyl acetate and washed with 1:2 water/brine, water and brine (×2). The organic phase was dried (MgSO4), filtered and concentrated to give the title compound (1.01 g, 97%), which was used without further purification. LCMS (PS-A2) Rt 4.07 min [M−H]− 355.

Provenance & Evidence