Dimethyl Disulfide → 3-Methyl-4-(methylthio)anisole

Participants

Reaction Steps

To the cold (−78° C.) solution of 2-bromo-5-methoxy toluene (8 g, 0.04 mol) in dry THF (80 mL) under inert atmosphere, butyl lithium solution (1.6M solution in hexane; 36.8 mL, 0.058 mol) was added dropwise and the mixture was stirred for 1 h at same temperature. Dimethyl disulphide (7.7 mL, 0.08 mol) was then added dropwise and the reaction mixture was allowed to warm to room temperature over a period of 2 h. The reaction mixture was quenched with sat. ammonium chloride solution and extracted in diethyl ether. The combined organic extracts were washed with water and brine and dried. The solvent was evaporated in vacuo to yield 6.5 g of 2-methyl-4-methoxy thioanisole, which was used as such in Step 2 MS m/z 168 (M+).

Provenance & Evidence