N-bromobutanimide → 3-bromo-9-(2-pyridinyl)-9H-Carbazole

Reaction equation

[Br:1]N1C(=O)CCC1=O.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N:15]1[C:27]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[C:21]2[C:16]1=[CH:17][CH:18]=[CH:19][CH:20]=2>CN(C=O)C.C1COCC1>[Br:1][C:24]1[CH:25]=[CH:26][C:27]2[N:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=3)[C:16]3[C:21]([C:22]=2[CH:23]=1)=[CH:20][CH:19]=[CH:18][CH:17]=3

Participants

Procedure

N-bromosuccinimide (17.8 g, 100 mmol) in DMF (50 mL) was added slowly to 9-(pyridin-2-yl)-9H-carbazole (24 g, 100 mmol) in THF (250 mL) at 0° C. over 30 min. The reaction was allowed to warm to room temperature and stir overnight. The reaction mixture was then evaporated and extracted with dichloromethane, and the organic layer was dried over magnesium sulfate and the solvent was then evaporated. The residue was then purified by column using toluene:hexane (1:1, v/v) as eluent and the product was further purified by recrystallization from toluene:ethanol (1:1, v/v), and after cooling, 24.3 g (75%) of the product was collected as a white solid after filtration.