Adipoyl chloride → 1,6-bis-[11-(2-ethylhexyl)-5-(2,4,6-trimethyl-benzoyl)-11H-benzo[a]-carbazol-8-yl]-hexane-1,6-dione

HRID 2203250Notes

Reaction equation

HRID 2203250 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:50])[CH2:43][CH2:44][CH2:45][CH2:46][C:47](Cl)=[O:48]>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:50])[CH2:43][CH2:44][CH2:45][CH2:46][C:47]([C:9]1[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:22][CH2:23][CH2:24][CH3:25])[C:17]1[C:12]3=[CH:13][C:14]([C:29](=[O:30])[C:28]3[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:27]=3[CH3:26])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=1)=[O:48])[CH:10]=2)[CH3:2]

Participants

6

Reactant 4

HCID 61034Adipoyl chlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole

Product 1

HCID 896280231,6-bis-[11-(2-ethylhexyl)-5-(2,4,6-trimethyl-benzoyl)-11H-benzo[a]-carbazol-8-yl]-hexane-1,6-dione

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (1.65 g; 5.00 mmol) in CH2Cl2 (15 mL) are added 2,4,6-trimethylbenzoyl chloride (0.92 g; 5.11 mmol) and AlCl3 (0.70 g; 5.25 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.70 g; 5.30 mmol) is added at 0° C. and adipoyl chloride (0.43 g; 2.33 mmol) is added dropwise, and then 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 water and brine, dried over MgSO4, and concentrated to give a green solid. The crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1) to give a beige solid (0.85 g; 34.4%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82 (t, 6H), 0.89 (t, 6H), 1.17-1.42 (m, 16H), 1.93 (br, 4H), 2.21 (s, 12H), 2.26 (m, 2H), 2.40 (s, 6H), 3.18 (br, 4H), 4.69 (m, 4H), 6.97 (s, 4H), 7.54 (d, 2H), 7.69-7.78 (m, 4H), 8.08 (s, 2H), 8.39 (s, 2H), 8.61 (br, 4H), 9.53 (d, 2H).

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 water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a green solid
  7. customThe crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1)
  8. customto give a beige solid (0.85 g; 34.4%)

Sources & evidence

ORD record
ord-17f2dcde0f5b4661aefdb693a757e1a8
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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