4-Fluorobenzoyl chloride → [11-(2-Ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)methanone

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Reaction Steps

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (10.0 g, 30.6 mmol) in CH2Cl2 (150 mL) are added 4-fluorobenzoyl chloride (5.03 g, 31.7 mmol) and AlCl3 (4.58 g, 34.3 mmol) at 0° C. After stirring for 0.5 hour, the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture is poured into ice-water, and the crude product is extracted with CH2Cl2. The organic layer is washed with water and brine, dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1) to obtain an off-white solid (8.14 g; 57%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.83 (t), 0.89 (t), 1.18-1.52 (m), 2.24-2.31 (m), 4.68-4.80 (m), 7.16 (t), 7.31 (t), 7.50 (t), 7.55-7.60 (m), 7.65 (t), 7.97 (dd), 8.06 (d), 8.31 (s), 8.50 (d), 8.65 (d); 19F-NMR spectrum (CDCl3). δ [ppm]−106.30.

Provenance & Evidence