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

HRID 2172367Notes

Reaction equation

HRID 2172367 reaction equation
[CH2:1]([CH:3]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22]([C:24]3[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=3)=[O:23])=[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].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:39][C:40]1[CH:48]=[C:47]([CH3:49])[CH:46]=[C:45]([CH3:50])[C:41]=1[C:42](Cl)=[O:43]>ClC1C=CC=CC=1>[CH2:1]([CH:3]([CH2:31][CH2:32][CH2:33][CH3:34])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:22](=[O:23])[C:24]3[CH:25]=[CH:26][C:27]([F:30])=[CH:28][CH:29]=3)=[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]([C:41]1[C:40]([CH3:39])=[CH:48][C:47]([CH3:49])=[CH:46][C:45]=1[CH3:50])=[O:43])[CH:10]=2)[CH3:2]

Participants

5

Reactant 3

HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 67130119[11-(2-Ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)methanone

Product 1

HCID 67130099[11-(2-Ethylhexyl)-5-(4-fluorobenzoyl)-11H-benzo[a]carbazol-8-yl]-(2,4,6-trimethylphenyl)-methanoneYield 52.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
65 °C

Procedure

To [11-(2-ethylhexyl)-11H-benzo[a]carbazol-5-yl]-(4-fluorophenyl)-methanone (2.00 g, 4.43 mmol) in chlorobenzene (12 mL) are added AlCl3 (1.24 g, 9.30 mmol) and 2,4,6-trimethylbenzoyl chloride (0.85 g, 4.65 mmol) at 0° C. After stirring for 2 hours at 65° C., 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 (4:1) to obtain a yellow solid (1.39 g, 52%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.83 (t), 0.92 (t), 1.19-1.47 (m), 2.13 (s), 2.26-2.35 (m), 2.35 (s), 4.74-4.78 (m), 6.93 (s), 7.16 (t), 7.56-7.59 (m), 7.67 (t), 7.93-7.98 (m), 8.28 (s), 8.36 (d), 8.55 (br), 8.62 (d); 19F-NMR spectrum (CDCl3). δ [ppm] −105.13.

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 (4:1)

Sources & evidence

ORD record
ord-fe380411dcde4a1d9319af8ce6119618
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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