Ethanol → 1-(Methylsulfinyl)-3-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

A solution of 3-nitro thioanisol (96 g, 568 mmol) in DCM (100 mL) is added dropwise to a cooled solution of sulfuryl chloride (96 g, 711 mmol) in DCM (600 mL) at −60° C. The mixture is stirred for 4 h at −20° C., then cooled to −60° C., and 350 mL of EtOH are carefully added. The reaction is then allowed to warm up to rt, subsequently, most of the solvent is evaporated, the residue is poured in sat. aq. NaHCO3, and the solid product is filtered off and carefully washed with hexane on the filter, then air-dried to give the desired sulfoxide (95 g, 90% yield).

Provenance & Evidence