o-Fluorobenzaldehyde → 2-(phenylsulfonyl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-fluorobenzaldehyde (4.67 g, 37.6 mmol), sodium benzenesulfinate (6.79 g, 41.3 mmol), and dimethylsulfoxide (30 mL) was heated at 95° C. for 18 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated to give a white solid. NMR analysis of this crude mixture indicated unreacted 2-fluorobenzaldehyde to be the major component. The crude mixture was redissolved in dimethylsulfoxide (30 mL), then sodium benzenesulfinate (5.0 g, 30 mmol) was added. The resulting mixture was heated at 95° C. for another 16 hours. The reaction mixture was cooled to room temperature, then partitioned between ethyl acetate and water. The organic phase was dried over MgSO4, filtered, and concentrated. A solution of this crude product and dichloromethane was evaporated over silica gel, and the resulting silica gel supported crude product was loaded onto an Analogix SuperFlash™ column. Flash chromatography (5%-35% ethyl acetate in hexanes) provided 1.96 g (23%) of 2-(benzenesulfonyl)-benzaldehyde as a clear, colorless oil which partially solidified over time.

Provenance & Evidence