2-Fluorobenzoyl chloride → 11-(2-Ethylhexyl)-8-(2-fluorobenzoyl)-11H-benzo[a]carbazole-5-yl-(2,4,6-trimethylphenyl)-methanone

HRID 2172359Notes

Reaction equation

HRID 2172359 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-].[F:42][C:43]1[CH:51]=[CH:50][CH:49]=[CH:48][C:44]=1[C:45](Cl)=[O:46]>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]([C:28]3[C:27]([CH3:26])=[CH:35][C:34]([CH3:36])=[CH:33][C:32]=3[CH3:37])=[O:30])=[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:45](=[O:46])[C:44]1[CH:48]=[CH:49][CH:50]=[CH:51][C:43]=1[F:42])[CH:10]=2)[CH3:2]

Participants

6

Reactant 4

HCID 98082-Fluorobenzoyl chlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole

Product 1

HCID 6809414611-(2-Ethylhexyl)-8-(2-fluorobenzoyl)-11H-benzo[a]carbazole-5-yl-(2,4,6-trimethylphenyl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (47.16 g; 143.0 mmol) in CH2Cl2 (400 mL) are added 2,4,6-trimethylbenzoyl chloride (27.45 g; 150.0 mmol) and AlCl3 (20.00 g; 150.0 mmol) at 0° C. After stirring at room temperature for 2 hours, AlCl3 (22.93 g; 172.0 mmol) is added at 0° C. and 2-fluorobenzoyl chloride (23.78 g; 150.0 mmol) is added dropwise, and then 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. After 230 ml of n-hexane is added there, CH2Cl2 was removed by concentration to give a beige solid. It is collected by filtration, and washed with n-hexane, and then it is dried to give a beige solid (81.81 g; 95.7%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.84 (t), 0.89 (t), 1.18-1.42 (m), 2.20 (s), 2.28-2.31 (m), 2.40 (s), 4.72-4.76 (m), 6.96 (s), 7.19 (t), 7.29 (t), 7.52-7.60 (m), 7.70-7.84 (m), 8.38 (s), 8.63-8.66 (m), 9.56 (d); 19F-NMR spectrum (CDCl3). δ [ppm]: −111.58

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. additionAfter 230 ml of n-hexane is added there
  6. customCH2Cl2 was removed by concentration
  7. customto give a beige solid
  8. filtrationIt is collected by filtration
  9. washwashed with n-hexane
  10. customit is dried
  11. customto give a beige solid (81.81 g; 95.7%)

Sources & evidence

ORD record
ord-56cd5b00dae94d0a94c774c06e182dfe
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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