Carbazole → 9-(4-Bromobutyl)-9H-carbazole

Participants

Reaction Steps

1,4-Dibromobutane (640.2 g, 30 mol) and sodium hydride (30.1 g, 0.60 mol, 55%) were mixed in 500 mL of DMF under an argon atmosphere. Carbazole (100.0 g, 0.60 mol) was slowly added and the reaction mixture was stirred for 6 hours at room temperature. DMF was removed by vacuum distillation. Then, 9-(4-bromobutyl)-9H-carbazole was purified in a fresh column. The resulting product was purified by silica gel column chromatography (eluent: ethyl acetate:hexane=1:50 v/v) to yield 112 g (62%) of 9-(4-bromobutyl)-9H-carbazole (Compound 8).

Provenance & Evidence