Acetyl chloride → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl}-ethanone

Participants

Reaction Steps

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (0.42 g; 1.27 mmol) in CH2Cl2 (20 mL) are added 2,4,6-trimethylbenzoyl chloride (0.23 g; 1.27 mmol) and AlCl3 (0.17 g; 1.27 mmol) at 0° C. After stirring at room temperature for 2.5 hours, acetyl chloride (0.17 g; 1.31 mmol) and AlCl3 (0.19; 1.40 mmol) are added at 0° C., and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a beige solid (0.45 g; 75%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82 (t, 3H), 0.90 (t, 3H), 1.18-1.45 (m, 6H), 2.20 (s, 6H), 2.29-2.30 (m, 1H), 2.41 (s, 3H), 2.72 (s, 3H), 4.74-4.77 (m, 2H), 6.98 (s, 2H), 7.58 (d, 1H), 7.70-7.79 (m, 2H), 8.10 (dd, 1H), 8.39 (s, 1H), 8.60 (d, 1H), 8.64 (d, 1H), 9.53 (d, 1H).

Provenance & Evidence