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

HRID 2172366Notes

Reaction equation

HRID 2172366 reaction equation
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.[Al+3].[Cl-].[Cl-].[Cl-].[F:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:17]([CH:5]([CH2:4][CH2:3][CH2:2][CH3:1])[CH2:6][N:8]1[C:7]2[C:15](=[CH:16][C:17]([C:27]([C:26]3[CH:30]=[CH:31][C:23]([F:22])=[CH:24][CH:25]=3)=[O:28])=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:16]

Participants

5

Reactant 3

HCID 9196Benzo[a]carbazoleHCID 678794-Fluorobenzoyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 67130119[11-(2-Ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)methanoneYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 11H-benzo[a]carbazole (8.24 g, 25.0 mmol) in CH2Cl2 (80 ml) are added AlCl3 (3.33 g, 25.0 mmol) and 4-fluorobenzoyl chloride (4.04 g, 25.5 mmol) at 0° C. After stirring at room temperature for 4 hours, the reaction mixture is poured into ice-water. The crude product is extracted with CH2Cl2, and washed with water and brine. After drying over MgSO4 and concentration, the crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:9) to obtain a yellow solid (4.96 g, 44%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82-0.91 (m), 1.18-1.47 (m), 2.21-2.30 (m), 4.67-4.78 (m), 7.16 (t), 7.30 (t), 7.50 (t), 7.55-7.59 (m), 7.63-7.67 (m), 7.96-8.00 (m), 8.05 (d), 8.31 (s), 8.51 (d), 8.63 (d); 19F-NMR spectrum (CDCl3). δ [ppm] −105.89.

Workup

  1. extractionThe crude product is extracted with CH2Cl2
  2. washwashed with water and brine
  3. dry with materialAfter drying over MgSO4 and concentration
  4. customthe crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:9)

Sources & evidence

ORD record
ord-db9dbd113a74443d9f84925d3b355908
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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