Carbazole → 9-(p-Tolyl)carbazole

HRID 1860357Notes

Reaction equation

HRID 1860357 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.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl.[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

7

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 122074-IodotolueneHCID 2855718-Crown-6

Product 1

HCID 157986519-(p-Tolyl)carbazoleYield 63.1%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

32.0 g (191 mmol) of carbazole, 50.0 g (229 mmol) of 4-iodotoluene, 2.02 g (31.9 mmol) of copper powder, 16.8 g (53.7 mmol) of 18-crown-6-ether and 29.0 g (210 mmol) of potassium carbonate were placed in a 500 ml four-necked flask with a mechanical stirrer and bulb-shaped cooler. To this was added 300 ml of o-dichlorobenzene as solvent. The resultant product was heated to 180° C. under a nitrogen flow in a silicone oil bath, and subjected to the reaction for 113 hours. After the reaction was completed, the reaction product was subjected to suction filtration with a suction funnel, before it was cooled down. The resultant filtrate was concentrated in an evaporator. To the resultant oily product was added 200 ml of methanol. The precipitated solid was subjected to the filtration at a reduced pressure with a suction funnel to obtain a gray solid, which was recrystallized in the presence of benzene to obtain 31.0 g of a white crystal.

Workup

  1. customsubjected to the reaction for 113 hours
  2. filtrationthe reaction product was subjected to suction filtration with a suction funnel, before it
  3. temperaturewas cooled down
  4. concentrationThe resultant filtrate was concentrated in an evaporator
  5. additionTo the resultant oily product was added 200 ml of methanol
  6. filtrationThe precipitated solid was subjected to the filtration at a reduced pressure with a suction funnel
  7. customto obtain a gray solid, which
  8. customwas recrystallized in the presence of benzene

Sources & evidence

ORD record
ord-255bdb06359944648afc3cd47df888cc
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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