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

HRID 37758Notes

Reaction equation

HRID 37758 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[F:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:37](Cl)(=[O:39])[CH3:38]>C(Cl)Cl>[C:37]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20](=[O:22])[CH3:21])=[CH:18][CH:19]=3)[C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][C:3]([C:28](=[O:29])[C:27]1[CH:31]=[CH:32][C:24]([F:23])=[CH:25][CH:26]=1)=[CH:2][CH:1]=3)(=[O:39])[CH3:38]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 99477551-[4-(9H-Carbazol-9-yl)phenyl]ethanone

Product 1

HCID 668864741-{4-[3-Acetyl-6-(4-fluoro-benzoyl)-carbazol-9-yl]-phenyl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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).

Workup

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with CH2Cl2
  3. washThe combined organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the residue, which
  7. customis purified
  8. washby washing with hot TBME (tert-butyl methyl-ether)
  9. customThe structure of the product, which is obtained as a white solid

Sources & evidence

ORD record
ord-50c9583c29da4b4a800f1cd5c5d6f1ba
Source dataset
uspto-grants-2013_09
Patent number
US08524425B2

Reaction notes

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