N-bromobutanimide → 3-Bromo-9-phenylcarbazole

Participants

Reaction Steps

Firstly, 24.3 g (100 mmol) of 9-phenylcarbazole was dissolved in 600 mL of glacial acetic acid, and 17.8 g (100 mmol) of N-bromosuccinimide was slowly added thereto. The mixture was stirred overnight at a room temperature. This glacial acetic acid solution was dropped into 1 L of ice water while stirring it. A precipitated white solid was washed with water three times. This solid was dissolved in 150 mL of diethyl ether, and washed with a saturated sodium hydrogen carbonate water solution and water. This organic phase was dried with magnesium sulfate, and filtered. The obtained filtrate was concentrated. About 50 mL of methanol was added to the obtained residue and uniformly dissolved therein. This solution was left still to precipitate a white solid. This solid was collected and dried to obtain 28.4 g (yield: 88%) of 3-bromo-9-phenylcarbazole, which was white powder.

Provenance & Evidence