Iodine → S-Methyl 4-methylbenzenesulfonothioate

Participants

Reaction Steps

In accordance with the method described in the literature (Synthesis 2002, 343), into a solution (12 mL) of 400 mg (4.25 mmoL) of dimethyl disulfide in methylene chloride were added 2.42 g (13.6 mmoL) of sodium p-toluenesulfinate and 2.16 g (8.50 mmoL) of iodine, followed by stirring at room temperature for 1 hour. The reaction solution was diluted with methylene chloride (12 mL), and a 1 M aqueous sodium thiosulfate solution was added thereto until the iodine color disappeared. The organic layer was washed with water (10 mL), dried over anhydrous magnesium sulfate, and filtered, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain 1.97 g of the heading compound as a colorless powdery substance (yield 100%).

Provenance & Evidence