3-Bromo-9H-carbazole

86-74-8

1592-95-6

General procedure for the synthesis of 3-bromocarbazole from carbazole: Carbazole (10 g, 59.80 mmol) was added to N,N-dimethylformamide (DMF, 67 mL) and stirred at room temperature for 15 min. A solution of N-bromosuccinimide (NBS, 10.6 g, 59.56 mmol) in DMF (100 mL) was slowly added dropwise at 0 °C. After the dropwise addition was completed, the reaction mixture was gradually warmed up to room temperature and stirring was continued for 2 hours. Upon completion of the reaction, the mixture was poured into water and a white precipitate precipitated. The precipitate was collected by filtration and dissolved in dichloromethane. The organic layer was washed with water to remove water soluble impurities. The organic phase was dried with anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent. The resulting white solid was purified by ethanol recrystallization to give 3-bromocarbazole in colorless crystalline form (10.65 g, 72% yield). The structure of the product was confirmed by 1H-NMR (CDCl3, 400 MHz) and mass spectrometry (ESI): 1H-NMR δ 8.34 (bs, 1H), 8.15 (d, J = 7.8 Hz, 1H), 7.48 (d, J = 8.2 Hz, 1H), 7.45 (m, 1H), 11.42 (s, 1H); MS (ESI) m/z 246 ( M+).