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Phenylacetyl chloride → 1-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanone

HRID 2172364
Notes
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Reaction equation

HRID 2172364 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-].[CH3:22][C:23]1[CH:31]=[C:30]([CH3:32])[CH:29]=[C:28]([CH3:33])[C:24]=1[C:25](Cl)=[O:26].[C:34]1([CH2:40][C:41](Cl)=[O:42])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=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:25](=[O:26])[C:24]3[C:23]([CH3:22])=[CH:31][C:30]([CH3:32])=[CH:29][C:28]=3[CH3:33])=[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]=[C:12]([C:41](=[O:42])[CH2:40][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH:13]=2)[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 7679Phenylacetyl chlorideHCID 9196Benzo[a]carbazoleHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×

Product 1

HCID 866905311-[11-(2-Ethylhexyl)-5-(2,4,6-trimethylbenzoyl)-11H-benzo[a]carbazol-8-yl]-2-phenyl ethanoneYield 159.5%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To 11H-benzo[a]carbazole (1.06 g, 3.23 mmol) in CH2Cl2 (5 ml) are added AlCl3 (0.510 g, 3.82 mmol) and 2,4,6-trimethylbenzoyl chloride (0.59 g, 3.24 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.51 g, 3.82 mmol) and phenylacetyl chloride (0.52 g, 3.39 mmol) are added at 0° C. The reaction mixture is stirred at room temperature for 2 hours, and then it 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 product is reprecipitated from CH2Cl2 and n-hexane to obtain a white powder (1.53 g, 81%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.79-0.91 (m), 1.18-1.50 (m), 2.19 (s), 2.28 (m), 2.41 (s), 4.38 (s), 4.74 (m), 6.97 (s), 7.22-7.36 (m), 7.56 (d), 7.71 (t), 7.77 (t), 8.14 (d), 8.35 (s), 8.62 (d), 8.63 (s), 9.58 (s).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 2 hours
  2. extractionThe crude product is extracted with CH2Cl2
  3. washwashed with water and brine
  4. dry with materialAfter drying over MgSO4 and concentration
  5. customthe product is reprecipitated from CH2Cl2 and n-hexane

Sources & evidence

ORD record
ord-2708f94ef57847c0879d48675562135a
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09051397B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes