Réaction #66036

Équation de réaction

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

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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