2-Methylbenzoyl chloride → 1-{4-[3,6-Bis-(2-methyl-benzoyl)-carbazol-9-yl]-phenyl}-ethanone

HRID 1429306Notes

Reaction equation

HRID 1429306 reaction equation
[CH:1]1[C:13]2[N:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20](=[O:22])[CH3:21])=[CH:16][CH:15]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:27]1([CH3:36])[C:28]([C:33](Cl)=[O:34])=[CH:29][CH:30]=[CH:31][CH:32]=1>C(Cl)Cl>[CH3:36][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[C:33]([C:8]1[CH:9]=[CH:10][C:11]2[N:12]([C:14]3[CH:15]=[CH:16][C:17]([C:20](=[O:22])[CH3:21])=[CH:18][CH:19]=3)[C:13]3[C:5]([C:6]=2[CH:7]=1)=[CH:4][C:3]([C:33](=[O:34])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:36])=[CH:2][CH:1]=3)=[O:34]

Participants

5

Reactant 3

HCID 702762-Methylbenzoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 99477551-[4-(9H-Carbazol-9-yl)phenyl]ethanone

Product 1

HCID 668829471-{4-[3,6-Bis-(2-methyl-benzoyl)-carbazol-9-yl]-phenyl}-ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-carbazol-9-yl-phenyl)-ethanone (2.0 g) in CH2Cl2 (100 mL) is added AlCl3 (3.3 g) and o-toluoyl chloride (2.3 g) at 0° C. After stirring overnight at room temperature, the reaction mixture is poured into ice-water. The product is extracted twice with CH2Cl2, and the combined organic layer is washed with H2O and brine, dried over MgSO4, and concentrated to give the residue, which is further dried in vacuo. The product thus obtained is used for the next reaction without further purification. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 2.35 (s, 6H), 2.72 (s, 3H), 7.26-7.38 (m, 6H), 7.40-7.46 (m, 4H), 7.70 (d, 2H), 7.97 (dd, 2H), 8.26 (d, 2H), 8.59 (d, 2H).

Workup

  1. extractionThe product is extracted twice with CH2Cl2
  2. washthe combined organic layer is washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give the residue, which
  6. customis further dried in vacuo
  7. customThe product thus obtained
  8. customis used for the next reaction without further purification

Sources & evidence

ORD record
ord-56396ce08fe940a7b8d15337e527776e
Source dataset
uspto-grants-2015_01
Patent number
US08940464B2

Reaction notes

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