Water → 5-Nitroindole

Participants

Reaction Steps

To a solution of 5-nitroindole (5.00 g, 30.8 mmol) in pyridine (200 mL) at −4° C. is added a solution of pyridinium bromide perbromide (10.99 g, 34.3 mmol) in pyridine (200 mL) dropwise under nitrogen with stirring. After complete addition, the reaction mixture is stirred for 5 min at 0° C. The reaction mixture is diluted in 0° C. water (200 mL) and extracted with 200 mL of Et2O. The organic layer is washed with 6 M HCl (300 mL), 5% NaHCO3 (300 mL), and brine (300 mL). The organic phase is dried over MgSO4 and solvent is removed to give 3-bromo-5-nitroindole as a yellow powder, 80% pure with 20% 5-nitroindole (6.80 g, 74% yield).

Provenance & Evidence