Acetyl chloride → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl}-ethanone

HRID 2172358Notes

Reaction equation

HRID 2172358 reaction equation
[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:2].[CH3:26][C:27]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:28]=1[C:29](Cl)=[O:30].[Al+3].[Cl-].[Cl-].[Cl-].[C:42](Cl)(=[O:44])[CH3:43]>C(Cl)Cl>[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:29](=[O:30])[C:28]3[C:27]([CH3:26])=[CH:35][C:34]([CH3:36])=[CH:33][C:32]=3[CH3:37])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:42](=[O:44])[CH3:43])[CH:10]=2)[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole

Product 1

HCID 671301181-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (0.42 g; 1.27 mmol) in CH2Cl2 (20 mL) are added 2,4,6-trimethylbenzoyl chloride (0.23 g; 1.27 mmol) and AlCl3 (0.17 g; 1.27 mmol) at 0° C. After stirring at room temperature for 2.5 hours, acetyl chloride (0.17 g; 1.31 mmol) and AlCl3 (0.19; 1.40 mmol) are added at 0° C., and the mixture is stirred at room temperature for 3 hours. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a beige solid (0.45 g; 75%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82 (t, 3H), 0.90 (t, 3H), 1.18-1.45 (m, 6H), 2.20 (s, 6H), 2.29-2.30 (m, 1H), 2.41 (s, 3H), 2.72 (s, 3H), 4.74-4.77 (m, 2H), 6.98 (s, 2H), 7.58 (d, 1H), 7.70-7.79 (m, 2H), 8.10 (dd, 1H), 8.39 (s, 1H), 8.60 (d, 1H), 8.64 (d, 1H), 9.53 (d, 1H).

Workup

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. extractionthe crude product is extracted twice with CH2Cl2
  3. washThe combined organic layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a beige solid (0.45 g; 75%)

Sources & evidence

ORD record
ord-f0b4362a2e0c4f859f631924639ffe9b
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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