Dimethyl Sulfide → (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride

Participants

Reaction Conditions

Reaction Steps

N-chlorosuccinimide (3.85 g, 29.35 mmole) was suspended in dichloroethane (40 ml) under a nitrogen atmosphere and cooled to −10° C. using an ice-salt-acetone bath. Dimethylsulfide (3 ml) was slowly added with stirring over a period of about 5 minutes. The mixture was stirred at this temperature for 10 minutes beyond the addition, at which time the ice-salt-acetone bath was replaced by a dry-ice acetone bath and the temperature was lowered to −50° C. To this solution was added 2-methylindole (3.85 g, 29.35 mmole) dissolved in dichloroethane (40 ml) slowly with stirring. The reaction mixture was stirred while allowing the temperature to reach 20° C. over about an hour. Diethyl ether (90 ml) was added with stirring and the precipitate which formed was filtered, washed well with ether, and dried overnight in a vacuum oven at room temperature. The free-flowing powder of (2-methyl-1H-indol-3-yl)-dimethylsulfonium chloride thus obtained was used without further purification in the following step.

Provenance & Evidence