2,4,6-Trimethylbenzoyl chloride → HCID 89615123, compound

HRID 2203252Notes

Reaction equation

HRID 2203252 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)[N:8]3[C:18]1[CH:23]=[CH:22][C:21]([C:24](=[O:26])[CH3:25])=[CH:20][CH:19]=1.[CH3:27][C:28]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:29]=1[C:30](Cl)=[O:31].[Al+3].[Cl-].[Cl-].[Cl-]>C(Cl)Cl>[CH3:27][C:28]1[CH:36]=[C:35]([CH3:37])[CH:34]=[C:33]([CH3:38])[C:29]=1[C:30]([C:17]1[CH:16]=[C:15]2[C:7]([N:8]([C:18]3[CH:19]=[CH:20][C:21]([C:24](=[O:26])[CH3:25])=[CH:22][CH:23]=3)[C:9]3[C:14]2=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:6]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=12)=[O:31]

Participants

5

Reactant 3

HCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 89614873HCID 89614873, compound

Product 1

HCID 89615123HCID 89615123, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-benzo[a]carbazol-11-yl-phenyl)-ethanone (649 mg, 1.93 mmol) in CH2Cl2 (10 mL) are added 2,4,6-trimethylbenzoyl chloride (369 mg, 2.02 mmol) and AlCl3 (1.50 g, 11.24 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 (383 mg; 41%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 2.22 (s), 2.41 (s), 2.77 (s), 6.97 (s), 7.15 (d), 7.30-7.34 (m), 7.39 (t), 7.51 (d), 7.63 (d), 7.65 (d), 8.01 (d), 8.28 (d), 8.28 (d), 8.39 (s), 9.53 (d).

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 (383 mg; 41%)

Sources & evidence

ORD record
ord-1e0364e24b184fe2aeba611302e70ec4
Source dataset
uspto-grants-2016_06
Patent number
US09365515B2

Reaction notes

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