Dimethylformamide → 5-Bromoindole-3-carbaldehyde

Participants

Reaction Steps

Dry DMF (7.5 ml) is cooled to 0° C. and treated dropwise with POCl3 (3.66 ml, 40 mmol). After stirring at this temperature for 15 min, a solution of 5-bromo-1H-indole (784 mg, 4 mmol) in dry DMF (2 ml) is added and the reaction mixture is allowed to warm to rt within 1 h. Stirring is continued at 40° C. for an additional hour, then the reaction mixture is cooled to rt and poured onto ice. Aqueous NaOH solution is added to neutralize the acidic solution, adjusting to pH 6. After stirring overnight at rt, the precipitate was collected by filtration, washed with water and dried under high vacuum to give pure subtitle compound (932 mg) as a beige solid in quantitative yield.

Provenance & Evidence