2-Thiophenecarbonyl chloride → (E)-1-[9-(4-Acetyl-phenyl)-6-(thiophene-2-carbonyl)-carbazol-3-yl]-but-2-en-1-one

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Reaction Steps

To 1-(4-carbazol-9-yl-phenyl)ethanone (30.0 g) in CH2Cl2 (1200 mL) is added thiophenecarbonyl chloride (15.4 g) and AlCl3 (28.4 g) at 0° C. After stirring overnight at room temperature, crotonyl chloride (11.3 g) and AlCl3 (15.5 g) are further added at 0° C. and the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with H2O and brine, dried over MgSO4, and concentrated to give the residue, which is purified by washing with hot ethyl acetate.

Provenance & Evidence