4-Fluorobenzoyl chloride → [11-(2-Ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)methanone

HRID 2203247Notes

Reaction equation

HRID 2203247 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].[F:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1.[Al+3].[Cl-].[Cl-].[Cl-]>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:31]([C:30]3[CH:34]=[CH:35][C:27]([F:26])=[CH:28][CH:29]=3)=[O:32])=[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]

Participants

5

Reactant 3

HCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole

Product 1

HCID 67130119[11-(2-Ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (10.0 g, 30.6 mmol) in CH2Cl2 (150 mL) are added 4-fluorobenzoyl chloride (5.03 g, 31.7 mmol) and AlCl3 (4.58 g, 34.3 mmol) at 0° C. After stirring for 0.5 hour, the reaction mixture is stirred for 2 hours at room temperature. The reaction mixture is poured into ice-water, and the crude product is extracted with CH2Cl2. The organic layer is washed with water and brine, dried over MgSO4. After concentration, the crude product is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1) to obtain an off-white solid (8.14 g; 57%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.83 (t), 0.89 (t), 1.18-1.52 (m), 2.24-2.31 (m), 4.68-4.80 (m), 7.16 (t), 7.31 (t), 7.50 (t), 7.55-7.60 (m), 7.65 (t), 7.97 (dd), 8.06 (d), 8.31 (s), 8.50 (d), 8.65 (d); 19F-NMR spectrum (CDCl3). δ [ppm]−106.30.

Workup

  1. stirringthe reaction mixture is stirred for 2 hours at room temperature
  2. extractionthe crude product is extracted with CH2Cl2
  3. washThe organic layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationAfter concentration
  6. customthe crude product is purified by column chromatography on silica gel eluting with a mixed solvent of n-hexane and CH2Cl2 (1:1)
  7. customto obtain an off-white solid (8.14 g; 57%)

Sources & evidence

ORD record
ord-a7c452dde84745afb3e55ac8b15416eb
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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