Carbazole → 9-(4-biphenylyl)carbazole

HRID 1993087Notes

Reaction equation

HRID 1993087 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:14]1[C:26]2[NH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]=2[CH:17]=[CH:16][CH:15]=1.CC(C)([O-])C.[Na+].C1(C)C(C)=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[CH-]1C(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=C1.[Fe+2].C1(C)C=CC=CC=1>[C:5]1([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:7][C:2]([N:25]2[C:26]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[C:19]3[C:24]2=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 71014-BromobiphenylHCID 7237O-XyleneHCID 23676156Sodium t-butoxide

Product 1

HCID 4128979-(4-biphenylyl)carbazoleYield 87.7%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 152416121,1`-Bis(diphenylphosphino)ferroceneCatalystHCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

12 g (50 mmol) of 4-bromobiphenyl, 8.4 g (50 mmol) of carbazole, 230 mg (1 mmol) of palladium acetate, 1.8 g (3.0 mmol) of 1,1-bis(diphenylphosphino)ferrocene, and 13 g (180 mmol) of sodium-tert-butoxide were put in a three-neck flask and the atmosphere of the flask was substituted by nitrogen, and then, 80 mL of dehydrated xylene was added thereto, and deaeration was performed. Under a nitrogen atmosphere, it was heated and stirred at 120° C. for 7.5 hours. After the termination of the reaction, about 600 mL of hot toluene was added to this suspension, and filtered twice through florisil, alumina, and Celite®. The obtained filtrate was concentrated, hexane was added thereto, and recrystallization was conducted. This was filtered, and the residue was collected and dried to obtain 14 g (yield: 87%) of 9-(4-biphenylyl)carbazole which was cream-colored powder.

Workup

  1. temperatureUnder a nitrogen atmosphere, it was heated
  2. additionwas added to this suspension
  3. filtrationfiltered twice through florisil, alumina, and Celite®
  4. concentrationThe obtained filtrate was concentrated
  5. additionhexane was added
  6. customrecrystallization
  7. filtrationThis was filtered
  8. customthe residue was collected
  9. customdried

Sources & evidence

ORD record
ord-7be14d803bbf4acca2ae31bf7b415425
Source dataset
uspto-grants-2010_01
Patent number
US07649197B2

Reaction notes

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