Carbazole → 9-(p-Tolyl)carbazole

HRID 1597732Notes

Reaction equation

HRID 1597732 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.I[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(C1C=CC=CC=1C(C)C)(C)C.[Cu]>[C:18]1([CH3:21])[CH:19]=[CH:20][C:15]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:16][CH:17]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 122074-Iodotoluene

Product 1

HCID 157986519-(p-Tolyl)carbazoleYield 76.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 11345Bis(1-methylethyl)benzeneSolvent

Procedure

10.0 g (59.8 mmol) of carbazole, 17.0 g (78.0 mmol) of 4-iodotoluene, 11.0 g (79.6 mmol) of potassium carbonate and 760 mg (12.0 mmol) of copper powder were allowed to react in 200 ml of diisopropylbenzene at 210° C. for 30 hours. The mixture was cooled to 80°-90° C., and filtered on sellaite. The filtrate was concentrated, and the residue was recrystallized from isopropanol to obtain 11.8 g of 9-p-tolylcarbazole.

Workup

  1. temperatureThe mixture was cooled to 80°-90° C.
  2. filtrationfiltered on sellaite
  3. concentrationThe filtrate was concentrated
  4. customthe residue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-83cfa187d4564cdcb07ec0b42833d31b
Source dataset
uspto-grants-1998_04
Patent number
US05736284

Reaction notes

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