3-Iodobenzaldehyde → 3-[(4-Bromophenyl)sulfonyl]benzaldehyde

Participants

Reaction Conditions

Reaction Steps

3-Iodobenzaldehyde (1.0 g, 4.3 mmol), copper(I) iodide (2.45 g, 12.9 mmol) and sodium 4-bromophenylsulfinate (1.55 g, 5.59 mmol) were combined in dimethylsulfoxide (8.6 mL) and heated to 110° C. for 4 hours. The cooled reaction mixture was diluted with ethyl acetate and filtered through Hyflo®. The filtrate was washed with water (×2) and brine and dried over MgSO4. The solvent was removed in vacuo and the residue purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to give 3-[(4-bromophenyl)sulfonyl]benzaldehyde (0.5 g, 35%). δH (400 MHz, d6 DMSO): 10.09 (1H, s), 8.47–8.44 (1H, m), 8.29–8.25 (1H, m), 8.21 (1H, d, J=7.6 Hz), 7.96–7.94 (2H, m), 7.88–7.84 (3H, m).

Provenance & Evidence