Carbazole → 9-Phenylcarbazole

HRID 1516994Notes

Reaction equation

HRID 1516994 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.Br[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(C)=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>[C:15]1([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:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 2855718-Crown-6

Product 1

HCID 708519-PhenylcarbazoleYield 97%

Reagents, catalysts & solvents 3

HCID 83681Tris(1,1-dimethylethyl)phosphineCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

Pd2(dba)3 (1.095 g, 1.196 mmol) and tri-tert-butylphosphine (4.78 ml, 4.78 mmol, 1.0 M in toluene) were mixed in 400 mL of xylene. The mixture was stirred under N2 for 20 min. 9H-carbazole (20 g, 120 mmol), bromobenzene (28.2 g, 179 mmol), 18-Crown-6 (3.16 g, 11.96 mmol), and potassium carbonate (24.80 g, 179 mmol) were then added in sequence, and the mixture was heated to reflux under N2 for 18 h. The xylene solution was decanted. The solvent was evaporated and residue was purified by vacuum distillation. 22.3 g (97% yield) of product was obtained after purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux under N2 for 18 h
  3. customThe xylene solution was decanted
  4. customThe solvent was evaporated
  5. distillationresidue was purified by vacuum distillation

Sources & evidence

ORD record
ord-45ba8d83575a46b693546cf6967d254e
Source dataset
uspto-grants-2012_07
Patent number
US08227801B2

Reaction notes

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