Reaction #66036

Reaction equation

acetyl chloride

AlCl3

1-(4-carbazol-9-yl-phenyl)-ethanone

p-fluorobenzoyl chloride

AlCl3

→

1-{4-[3-Acetyl-6-(4-fluoro-benzoyl)-carbazol-9-yl]-phenyl}-ethanone

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred at room temperature overnight
2. 2
   Extractionthe crude product is extracted twice with CH2Cl2
3. 3
   WashThe combined organic layer is washed with H2O and brine
4. 4
   Dryingdried over MgSO4
5. 5
   Concentrationconcentrated
6. 6
   Otherto give the residue, which
7. 7
   Otheris purified
8. 8
   Washby washing with hot TBME (tert-butyl methyl-ether)
9. 9
   OtherThe structure of the product, which is obtained as a white solid

Procedure

To 1-(4-carbazol-9-yl-phenyl)-ethanone (5.71 g) in CH2Cl2 (150 mL) is added p-fluorobenzoyl chloride (3.17 g) and AlCl3 (5.41 g) at 0° C. After stirring overnight at room temperature, acetyl chloride (1.73 g) and AlCl3 (2.93 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 TBME (tert-butyl methyl-ether). The structure of the product, which is obtained as a white solid, is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.73 (s, 3H), 2.75 (s, 3H), 7.23 (t, 2H), 7.48 (d, 1H), 7.51 (d, 1H), 7.72 (d, 2H), 7.91 (dd, 2H), 7.99 (d, 1H), 8.14 (d, 1H), 8.28 (d, 2H), 8.66 (s, 1H), 8.80 (s, 1H).

Source