Carbazole → 9-(8-Bromodibenzo[b,d]furan-2-yl)-9H-carbazole

Participants

Reaction Conditions

Reaction Steps

A mixture of carbazole (1.15 g, 6.87 mmol), 2,8-dibromodibenzo[b,d]furan (4.48 g, 13.74 mmol), copper powder (0.30 g, 4.58 mmol), potassium carbonate (3.80 g, 27.50 mmol), 18-crown-6 (0.61 g, 2.29 mmol), and 1,2-dichlorobenzene (50 mL) was degassed with bubbling argon for 45 min at 50° C. The reaction mixture was then heated to 200° C. and was stirred overnight (45 hours), maintaining an argon atmosphere. Production of decoupled material was shown by LCMS and the reaction was cooled to room temperature. The mixture was filtered, and the filtrate was dried. The copper was removed by a short silica gel plug with dichloromethane as the eluent, and the product was purified by silica gel column chromatography with toluene in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 12 (0.861 g, 30%). Confirmed by LCMS (APCI): calculated for C24H14BrNO (M+H): 412. Found: 412.

Provenance & Evidence