Dimethyl Sulfoxide → 2,1-Benzisothiazole-4-carboxaldehyde

Participants

Reaction Steps

Under nitrogen atmosphere, dimethyl sulfoxide (10.8 mL, 153 mmol) was added to a solution of oxalyl chloride (6.68 mL, 76.0 mmol) in dichloromethane (200 mL) at −78° C., and the mixture was stirred for 30 min. To the reaction mixture was added a solution of 2,1-benzisothiazol-4-ylmethanol (4.20 g, 25.4 mmol) in dichloromethane (54 mL), and the mixture was stirred for 2 hr. To the reaction mixture was added triethylamine (32.2 mL, 229 mmol) at −78° C., and the mixture was stirred for 1 hr. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=20/80) to give the title compound (3.94 g, yield 95%).

Provenance & Evidence