9-(8-bromooctyl)carbazole synthesis

Yield:127271-60-7 80%

Reaction Conditions:

Stage #1: 9H-carbazolewith potassium carbonate in N,N-dimethyl-formamide at 110; for 2 h;
Stage #2: 1,8-dibromooctane in N,N-dimethyl-formamide at 110; for 12 h;

Steps:

1.4 4.1.1.4. 9-(8-Bromooctyl)-9H-carbazole (5)

9H-Carbazole (5 g,29.9 mmol), K2CO3 (20.66 g, 149.52 mmol) were solved in 60 mL N,N-dimethylformamide, then the mixture was stirred for 2 h at110 C. Then 1,8-dibromooctane (24.40 g, 89.71 mmol) was addedinto reaction vessel, and stirring at 110 C for 12 h. The mixturewasextracted 3 times by using dichloromethane. After removing theorganic phase under reduced pressure, the crude product was purifiedby column chromatography with a yield of 80%. 1H NMR(500 MHz, CDCl3) d (ppm) 8.11 (d, J 7.7 Hz, 2H), 7.47 (m, 2H), 7.41(d, J 8.2 Hz, 2H), 7.25e7.20 (m, 2H), 4.31 (t, J 7.2 Hz, 2H), 3.38 (t,J 6.8 Hz, 2H), 1.94e1.73 (m, 4H), 1.34 (m, 8H).

References:

Zhao, Sen;Liang, Junfei;Guo, Ting;Wang, Yu;Chen, Xuan;Fu, Denghao;Xiong, Junbin;Ying, Lei;Yang, Wei;Peng, Junbiao;Cao, Yong [Organic electronics,2016,vol. 38,p. 130 - 138]