Carbazole → 1-Phenyl-9H-carbazole

HRID 1672106Notes

Reaction equation

HRID 1672106 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][CH:18]=[CH:17][CH:16]=1.C(O[Na])(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C(C)=CC=CC=1>[C:15]1([C:10]2[C:11]3[NH:12][C:13]4[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=4)[C:6]=3[CH:7]=[CH:8][CH:9]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 11575IodobenzeneHCID 178418730sodium 2-methylpropan-2-olate

Product 1

HCID 134974741-Phenyl-9H-carbazole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7237O-XyleneSolvent

Procedure

Under an argon stream, 670 g of carbazole, 850 kg of iodobenzene, 20 L of xylene, 460 g of t-BuONa, and palladium acetate (Pd (OAc)) were charged, and the mixture was refluxed for 8 hours. Impurities were filtered and the filtrate was concentrated under reduced pressure, followed by washing with hexane and drying, whereby phenylcarbazole was obtained as 820 g of white powder. The same reaction as in the synthesis of Intermediate 1 was carried out except that phenylcarbazole was used instead of 4-bromobiphenyl, whereby 650 g of white powder was obtained. By an FD-MS analysis, the white powder was identified as Intermediate 14.

Workup

  1. temperaturethe mixture was refluxed for 8 hours
  2. filtrationImpurities were filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. washby washing with hexane
  5. customdrying

Sources & evidence

ORD record
ord-bd7d3bf121344552809af7401df8c479
Source dataset
uspto-grants-2011_08
Patent number
US07998596B2

Reaction notes

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