2-Bromothiophene → Carbazole

Participants

Reaction Steps

A mixture of 1,5-dihexyl-3,7-di-(5-bromothiophen-2-yl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (0.150 g, 0.221 mmol), 2,7-bis(4′,4′,5′,5′-tetramethyl-1′,3′,2′-dioxaborolan-2′-yl)-N-9″i-heptadecanylcarbazole (0.152 g, 0232 mmol), Pd2(dba)3 (5.0 mg), (o-tol)3P (3.0 mg), K3PO4 (0.187 g) and toluene/H2O (20 mL/1 mL) was heated at reflux for 24 h. 2-bromothiophene (0.035 g, 0.22 mmol) in toluene (1 mL) was added and the resulting mixture was stirred for another 12 h. Then, after cooling to room temperature, the mixture was dropped into methanol to precipitate. After being filtered and dried, the precipitation was Soxhlet extracted with methanol, acetone, hexane, dichloromethane. A black solid (0.170 g, 85%) was obtained.

Provenance & Evidence