N-bromobutanimide → 3-Bromo-9-phenylcarbazole

Participants

Reaction Steps

24.3 g (100 mmol) of N-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 for about 12 hours 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 solution and water. This organic layer was dried with magnesium sulfate. A mixture is filtered and a filtrate was concentrated. When an obtained residue was recrystallized with methanol, 28.4 g of 3-bromo-9-phenylcarbazole that was a target substance and was white powder was obtained in a yield of 88% (Synthesis Scheme (c-1)).

Provenance & Evidence