N-bromobutanimide → 3-Bromo-9-phenylcarbazole

Participants

Reaction Steps

24.3 g (100 mmol) of 9-phenylcarbazole was put into a 2 L Meyer flask, and dissolved in 600 mL of glacial acetic acid. Then, 17.8 g (100 mmol) of N-bromosuccinimide was slowly added thereto, and the solution was stirred at room temperature for about 12 hours. This glacial acetic acid solution was dropped into 1 L of ice water while being stirred. A white solid substance precipitated was collected by suction filtration, and then washed with water three times. This solid substance was dissolved in 150 mL of diethyl ether, and the solution was washed with a saturated sodium hydrogen carbonate aqueous solution and then with water. The organic layer was dried with magnesium sulfate, the mixture was filtered by suction filtration, and the filtrate was concentrated. Thus, an oily substance was obtained. The oily substance was dissolved in about 50 mL of methanol. A precipitate of a white solid substance was produced by keeping this solution still. This solid substance was collected by suction filtration and dried. Then, 28.4 g (88% yield) of 3-bromo-9-phenylcarbazole was obtained as white powder.

Provenance & Evidence