Dimethyl Sulfoxide → 3-(TRIFLUOROMETHYLTHIO)BENZALDEHYDE

Participants

Reaction Conditions

Reaction Steps

Add a solution of dimethyl sulfoxide (0.82 mL, 11.5 mmol) in dichloromethane (2 mL) over a period of 5 minutes to a solution of oxalyl chloride (0.46 mL, 5.28 mmol) in dichloromethane (10 mL) cooled to −78° C. Stir 10 minutes then add a solution of (3-trifluoromethylsulfanyl-phenyl)-methanol (1.00 g, 4.80 mmol) in dichloromethane (4 mL). Stir 15 minutes then add triethylamine (3.35 mL, 24.0 mmol). Slowly warm to ambient temperature, add water and separate the organic layer. Extract the aqueous layer with dichloromethane. Dry (sodium sulfate) the combined organic layers, filter, and concentrate in vacuo. Purify by silica gel chromatography (10% ethyl acetate/hexane) to afford the titled compound as a yellow liquid (896 mg, 91%). 1H NMR (400 MHz, DMSO) δ 7.74 (dd, J=7.6, 7.6, 1H), 8.01 (d, J=7.9, 1H), 8.09 (d, J=7.5, 1H), 8.12 (s, 1H), 10.03 (s, 1H).

Provenance & Evidence