1,2-Dibromobenzene → 3-(2-Bromophenyl)-9-phenyl-9H-carbazole

HRID 1808690Notes

Reaction equation

HRID 1808690 reaction equation
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1Br>O1CCOCC1.C(OCCO)C.C(=O)([O-])[O-].[Na+].[Na+].C1(P([Pd-4](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:16]1[CH:17]=[CH:18][C:19]2[N:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[C:8]3[C:13]([C:14]=2[CH:15]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

Participants

7

Reactant 2

HCID 114141,2-DibromobenzeneHCID 513584509-Phenyl-9H-carbazole-3-boronic acid

Product 1

HCID 669295403-(2-Bromophenyl)-9-phenyl-9H-carbazole

Reagents, catalysts & solvents 4

HCID 178420553HCID 178420553, compoundCatalystHCID 8076Glycol monoethyl etherSolventHCID 10340Sodium CarbonateSolventHCID 312751,4-DioxaneSolvent

Procedure

1.1 g (1 mmol) of tetrakis(triphenylphosphino)palladium(0) are added to a mixture of 28.7 g (100 mmol) of N-phenylcarbazole-3-boronic acid, 36.1 ml (300 mmol) of 1,2-dibromobenzene in 150 ml of dioxane, 100 ml of 2-ethoxyethanol and 250 ml of 2 N sodium carbonate solution, and the mixture is heated under reflux for 16 h. After cooling, the organic phase is separated off, 500 ml of toluene are added, and the mixture is washed three times with 500 ml of water, dried over magnesium sulfate, filtered through silica gel and then freed from toluene and excess 1,2-dibromobenzene in vacuo. The residue is washed by stirring three times with hot ethanol. Yield: 26.7 g (67 mmol), 67.1%, purity 97% according to

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux for 16 h
  3. temperatureAfter cooling
  4. customthe organic phase is separated off
  5. addition500 ml of toluene are added
  6. washthe mixture is washed three times with 500 ml of water
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered through silica gel
  9. washThe residue is washed

Sources & evidence

ORD record
ord-3f3fc7a08fba4a14a48ca9433b59d217
Source dataset
uspto-grants-2013_01
Patent number
US08361638B2

Reaction notes

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