Carbazole → 9-Phenylcarbazole

HRID 1247706Notes

Reaction equation

HRID 1247706 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.CC(C)([O-])C.[Na+].Br[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C2(C3C=CC=CC=3)CC2(P(C(C)(C)C)C(C)(C)C)C)C=CC=CC=1>[C:21]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:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 7961BromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 708519-PhenylcarbazoleYield 98.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 21909131Di-tert-butyl(1-methyl-2,2-diphenylcyclopropyl)phosphaneCatalystHCID 7237O-XyleneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of carbazole (0.34 g, 2.0 mmol) in xylene (4 ml) were added sodium tert-butoxide (0.23 g, 2.4 mmol), bromobenzene (0.23 ml, 2.2 mmol), palladium acetate (4.5 mg, 0.02 mmol) and 2,2-diphenyl-1-(di-tert-butylphosphino)-1-methylcyclopropane (14.1 mg, 0.04 mmol) obtained in Example 4 under a nitrogen atmosphere and the mixture was stirred for 3 hours at 120° C. The reaction mixture was cooled, washed with water, and dried over anhydrous magnesium sulfate. Then, the solvent was removed under reduced pressure, and the concentrate was purified by column chromatography to give N-phenylcarbazole (0.479 g, 98%, purity: >99%) as white crystal.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThen, the solvent was removed under reduced pressure
  5. customthe concentrate was purified by column chromatography

Sources & evidence

ORD record
ord-6856358251524857ae1fff82e822318b
Source dataset
uspto-grants-2006_10
Patent number
US07129367B2

Reaction notes

Loading…