Sodium Thiosulfate → 1-(Cyclopropanesulfinyl)-4-nitrobenzene

Participants

Reaction Steps

179 mg (1.11 mmol) of iron(III) chloride was added to a mixture of 7.2 g (36.88 mmol) of 1-cyclopropylsulfanyl-4-nitrobenzene in 140 ml acetonitrile and it was stirred for 15 minutes at room temperature. Then 9.25 g (40.57 mmol) of periodic acid was added in portions at 25° C. The mixture was stirred for 30 minutes and then added, while stirring, to a cooled saturated sodium thiosulfate solution. It was then extracted with ethyl acetate (2×). The combined organic phases were dried (Na2SO4), filtered and concentrated by evaporation. The residue obtained was purified chromatographically (hexane/ethyl acetate 1:1). 5.93 g (28.07 mmol; yield: 76%) of the product was obtained.

Provenance & Evidence