Dimethylformamide → 4-Bromo-1H-indole-3-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

POCl3 (1.02 g, 6.63 mmol) was added dropwise to ice cold DMF (3 mL) and stirred for 15 min. 4-Bromoindole (1.00 g, 5.10 mmol) in DMF (1 mL) was added slowly. The mixture was heated to 35° C. with continuous stirring for 1.20 h (yellow precipitation was formed). The reaction mixture was cold on ice and treated with ice and 20% W/w aq. NaOH to pH 14 (pink color). Heating at reflux for 15 min. afforded a yellow clear solution, which formed a white precipitation when allowed to attain rt. The precipitation was filtered off, rinsed with ice cold water and dried under reduced pressure over weekend to give the title compound (1.14 g, 65%) as an off white solid. MS (ESI+) for C9H6BrNO m/z 224 (M+H)+.

Provenance & Evidence