Benzenesulfonyl chloride → 1-(benzenesulfonyl)-1H-indole-5-carbaldehyde

Participants

Reaction Steps

To a solution of 1H-indole-5-carbaldehyde CCLXIII (2.00 g, 13.778 mmol, 1 eq.) in dichloromethane (40 mL) was added, at room temperature, tetrabutylammonium hydrogen sulfate (0.1 eq.) followed by a solution of sodium hydroxide (10.0 eq.) in water (20 mL). Phenylsulfonyl chloride (1.2 eq.) was then slowly added and the resulting mixture was stirred at room temperature for 4 hours. The reaction mixture was then diluted with water and extracted with dichloromethane. The combined organic extracts were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (EtOAc/hexane, 20/80 to 35/65) to give 3.671 g (93% yield) of 1-benzenesulfonyl-1H-indole-5-carbaldehyde CCLXIV as a white solid.

Provenance & Evidence