5-Bromoindole → Indole-5-carbonitrile

Participants

Reaction Steps

CuCN (3.7 g, 40.70 mmol) was added to a solution of 5-bromo-1H-indole (5 g, 25.26 mmol) in 1-methylpyrrolidin-2-one (25 mL), and the resulting solution was stirred at reflux for 18 hours. The reaction mixture was then added to 200 g of ice and the mixture was filtered. The filter cake was washed with ammonium hydroxide (3×50 mL). The residue was dissolved in chloroform (600 mL) and then filtered. The organic layer was washed with water (200 mL), and dried (MgSO4). After a further filtration, the filtrate was concentrated to yield 3.7 g (82%) of 1H-indole-5-carbonitrile as brown oil.

Provenance & Evidence