Carbazole → 9-(4-Methoxyphenyl)carbazole

HRID 1860350Notes

Reaction equation

HRID 1860350 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]([O:21][CH3:22])=[CH:17][CH:16]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=CC=CC=1Cl.[Cu]>[CH3:22][O:21][C:18]1[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 2855718-Crown-6HCID 696764-Iodoanisole

Product 1

HCID 31108029-(4-Methoxyphenyl)carbazoleYield 45.3%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

8.10 g (48.5 mmol) of carbazole, 12.50 g (53.4 mmol) of 4-iodoanisole, 0.38 g (6.08 mmol) of copper powder, 4.28 g (16.2 mmol) of 18-crown-6-ether and 7.24 g (53.4 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 100 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 24 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 ethanol. 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 6.0 g of a white crystal.

Workup

  1. customsubjected to the reaction for 24 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 ethanol
  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-7adf12eacc2149c5bd69c59c397d2fd7
Source dataset
uspto-grants-2003_03
Patent number
US06528657B2

Reaction notes

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