Toluene → 4-broMo-9-phenyl-9H-carbazole

HRID 1065988Notes

Reaction equation

HRID 1065988 reaction equation
C1(C)C=CC=CC=1.CC(C)([O-])C.[Na+].[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.Br[C:28]1[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][CH:29]=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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2].O.CCOCC>[Br:34][C:31]1[C:32]2[C:23]3[C:24](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:25]([C:26]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:33]=2[CH:28]=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 6854Carbazole2×HCID 78041,4-DibromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 211973044-broMo-9-phenyl-9H-carbazole

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 21584184Diethylether waterSolvent

Conditions

Temperature
100 °C

Procedure

A reaction vessel was charged with 4.37 mmol (4.00 g) Pd2dba3, (dba=dibenzoylacetone), 6.55 mmol (3.63 g) dppf (dppf=diphenylphosphine ferrocene), and 400 ml dry toluene. Using a magnetic stir bar and hot plate, the mixture was stirred for 15 minutes under argon. Then 436 mmol (48.92 g) sodium t-butoxide was added against counter flow of argon and the reaction was stirred another 30 minutes. Then 291 mmol (48.66 g) carbazole with 873 mmol (205.96 g) 1,4-dibromobenzene were added and the reaction was heated to 100° C. for 16 hours. The reaction progress was followed by TLC until no carbazole could be detected. At end of reaction, the reaction mixture was taken up into water/ether (2:1). The mixture was then washed with water until the organic layer was colorless, then the solution was concentrated. The residue was dissolved in a mixture of toluene/hexane and passed through a short column of silica gel. The solvent was then removed from the column filtrate which yielded the product.

Workup

  1. stirringthe reaction was stirred another 30 minutes
  2. customAt end of reaction
  3. washThe mixture was then washed with water until the organic layer
  4. concentrationthe solution was concentrated
  5. dissolutionThe residue was dissolved in a mixture of toluene/hexane
  6. customThe solvent was then removed from the column filtrate which
  7. customyielded the product

Sources & evidence

ORD record
ord-9eb79bb0dc924dc18e0bd4671a447ca9
Source dataset
uspto-grants-2001_06
Patent number
US06242115B1

Reaction notes

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