90% |
|
9-Heptadecanyl-2,7-dibromocarbazole (9): 2,7-dibromo-9-H-carbazole (4 g, 12 mmol) and potassium hydroxide (0.84 g, 17.8 mmol) were solubilized in dry DMSO (40 mL). The reaction mixture was heated at 80 C for 1 h before adding dropwise a solution of 9-Heptadecane p-toluenesulfonate (6.4 g, 15.6 mmol) in 60 mL of dry DMSO. After cooling down at room temperature, the reaction mixture was poured into 300 mL of water and extracted three times with 100 mL of diethylether, dried over magnesium sulfate and the solvent was removed under vacuum. The white powder was purified by flash chromatography in cyclohexane to afford white crystals (yield: 90%). 1H NMR (400 MHz, CDCl3): delta (ppm) 7.5 (s, 2H); 7.27 (s, 2H); 7.12 (m, 2H), 4.48 (tt, J = 10.1, 5.1 Hz, 1H); 2.20 (m, 2H); 1.83 (m, 2H) 1.32-1.02 (m, 28H); 0.83 (t, J = 7.0 Hz, 6H). 13C NMR (100 MHz, CDCl3): delta (ppm) 125.61; 125.23; 120.43; 118.54; 111.70, 108.87, 56.43; 33.85; 31.89; 29.53; 29.43; 29.30; 26.94; 22.73; 14.20. HRMS (EI+, m/z) [M]+ calculated (%) for C29H41Br2N: 561.16057, found 561.16261. |
78% |
With potassium hydroxide; In dimethyl sulfoxide; for 24h; |
After loading the compound f-2 (1g) To a round flask, place the compound 4-f (1.9g, 1.5eq). And after inserting the KOH (1g, 5eq) above, it is injected DMSO as a solvent. And then stirred for 24 hours, the organic layer was extracted with MC and the salt water to remove the remaining water over anhydrous magnesium sulfate and, after evaporation of the solvent was recrystallized from a MC and MeOH as a white solid 2,7-dibromo-9- (heptadecane and the -9-yl) -9H-carbazole (compound f-5) obtained. (Yield: 78%) |