2-Methylbenzoyl chloride → HCID 66980798, compound

HRID 2172370Notes

Reaction equation

HRID 2172370 reaction equation
[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]1=2)[CH3:2].[Al+3].[Cl-].[Cl-].[Cl-].[CH3:30][C:31]1[CH:39]=[C:38]([CH3:40])[CH:37]=[C:36]([CH3:41])[C:32]=1[C:33](Cl)=[O:34].[C:42]1([CH3:51])[C:43]([C:48](Cl)=[O:49])=[CH:44][CH:45]=[CH:46][CH:47]=1>C(Cl)Cl>[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[CH:16]=[CH:15][C:14]3[CH:18]=[C:19]([C:33](=[O:34])[C:32]4[C:31]([CH3:30])=[CH:39][C:38]([CH3:40])=[CH:37][C:36]=4[CH3:41])[CH:20]=[CH:21][C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([C:48]([C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=3[CH3:51])=[O:49])[CH:8]=[CH:7][C:6]1=2)[CH3:2]

Participants

6

Reactant 4

HCID 702762-Methylbenzoyl chlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2×HCID 66980816HCID 66980816, compound

Product 1

HCID 66980798HCID 66980798, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-(2-ethylhexyl)-7H-benzo[c]carbazole (0.66 g, 2.00 mmol) in CH2Cl2 are added AlCl3 (0.27 g, 2.06 mmol) and 2,4,6-trimethylbenzoyl chloride (0.37 g, 2.00 mmol) at 0° C., and then the mixture is stirred for 2 hours. To the reaction mixture are added AlCl3 (0.29 g, 2.20 mmol) and o-toluoyl chloride (0.32 g, 2.06 mmol) at 0° C., and then the mixture is stirred overnight. The reaction mixture is poured into ice-water, and 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 white solid (0.25 g, 21%). The structure is confirmed by 1H-NMR spectrum (CDCl3) δ [ppm]: 0.84 (t), 0.93 (t), 1.22-1.45 (m), 2.04-2.09 (m), 2.18 (s), 2.38 (s), 2.39 (s), 4.32-4.34 (m), 6.97 (s), 7.30-7.37 (m), 7.42-7.47 (m), 7.51 (d), 7.68 (d), 7.88 (br), 7.96 (d), 8.21 (dd), 8.37 (d), 8.78 (br), 9.19 (br).

Workup

  1. stirringthe mixture is stirred overnight
  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 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-83ad1cd504ae424b932ba407b5ef036c
Source dataset
uspto-grants-2015_06
Patent number
US09051397B2

Reaction notes

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