Bromochloromethane → 5-Chloromethylthio-1-methyltetrazole

Participants

Reaction Steps

To a solution of 1-methyltetrazole-5-thiol sodium salt (2.00 g : 14.5 mMol.) in dimethylformamide (20 ml) under ice cooling is added bromochloromethane (20 ml) in one portion, and the mixture is stirred for 1.5 hour. The reaction mixture is diluted with water and extracted with ethyl acetate. The extract is washed with brine, dried over sodium sulfate, filtered, and concentrated. The residue is purified by silica gel column chromatography (toluene : ethyl acetate=20:1-10:1) to give 5-chloromethylthio-1-methyltetrazole as colorless crystals (1.73 g). Yield : 72%, m.p. 55° to 56° C.

Provenance & Evidence