Carbazole → 9-Phenylcarbazole

HRID 923700Notes

Reaction equation

HRID 923700 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.[O-]CCCC.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[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

7

Reactant 4

HCID 6854CarbazoleHCID 7961BromobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23669364Sodium n-butylate

Product 1

HCID 708519-Phenylcarbazole

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
60 °C

Procedure

2.5 g of carbazole, 2 g of bromobenzene and 0.064 g of a palladium acetate catalyst were dissolved in 40 mL of toluene, and the resulting solution was heated to 60° C. Subsequently, a solution of 1.5 g of sodium butoxide and 0.385 g of tri-tert-butylphosphine dissolved in toluene was slowly added dropwise. The mixture was refluxed at a steady 100° C. After completion of the reaction, the reaction mixture was extracted with dichloromethane and distilled water, and the solvent was dried. The resulting solid was filtered and purified, yielding a 9-phenyl carbazole compound as an intermediate.

Workup

  1. additionwas slowly added dropwise
  2. temperatureThe mixture was refluxed at a steady 100° C
  3. customAfter completion of the reaction
  4. extractionthe reaction mixture was extracted with dichloromethane
  5. distillationdistilled water
  6. customthe solvent was dried
  7. filtrationThe resulting solid was filtered
  8. custompurified

Sources & evidence

ORD record
ord-5fdf4fe57b5a41bbac26ed7cd82381d5
Source dataset
uspto-grants-2016_03
Patent number
US09278986B2

Reaction notes

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