N-bromobutanimide → 3-Bromo-9-phenylcarbazole

Participants

Reaction Steps

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

Provenance & Evidence