N-bromobutanimide → 3-Bromo-9-phenylcarbazole

Participants

Reaction Steps

First, 24.3 g (100 mmol) of N-phenylcarbazole was dissolved in 600 mL of glacial acetic acid, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added therein, and the mixture was stirred at room temperature for 18 hours. This reaction solution was dripped to 1 L of ice water while being stirred, and a white solid which was precipitated was washed with water three times. The obtained solid was dissolved in 150 mL of diethyl ether and washed with a saturated sodium hydrogen-carbonate aqueous solution and water. After being washed, an organic layer was dried with magnesium sulfate. After filtration, the filtrate was concentrated. Thereafter, approximately 50 mL of methanol was added to an obtained solid, and the solid was irradiated with ultrasonic waves to be uniformly dissolved. This solution was left at rest, and a white precipitate was obtained. This precipitate was collected by filtration and dried; thus, 28.4 g of a white powder of 3-bromo-9-phenylcarbazole that was an object was obtained (yield: 88%).

Provenance & Evidence