Iodine → 6-fluoro-3-iodo-1H-indole

Participants

Reaction Steps

To a solution of 6-fluoroindole (1.14 g, 8.44 mmol) in DMF (20 mL) was added potassium hydroxide (0.521 g, 9.28 mmol) at 0° C. The resulting mixture was stirred at 0° C. for 10 minutes before the addition of iodine (2.57 g, 10.1 mmol). After stirring at room temperature with protection from light for 18 hours, the reaction was diluted with saturated sodium bicarbonate. The aqueous mixture was extracted three times with EtOAc. The combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography (5% MeOH in DCM) to give 3-iodo-6-fluoroindole as a red solid (1.44 g, 65.4%).

Provenance & Evidence