Carbazole → 9-(4-Bromophenyl)carbazole

HRID 1816863Notes

Reaction equation

HRID 1816863 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:14][C:15]1[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=1.CC(C)([O-])C.[Na+].CC1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCC.C1(C)C=CC=CC=1.CCCCCC>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([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:17][CH:16]=1

Participants

8

Reactant 4

HCID 6854CarbazoleHCID 7237O-XyleneHCID 78041,4-DibromobenzeneHCID 23676156Sodium t-butoxide

Product 1

HCID 223613909-(4-Bromophenyl)carbazoleYield 44.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 8058HexaneSolventHCID 21889329Toluene hexaneSolvent

Procedure

4.30 g (25.7 mmole) of carbazole, 18.19 g (77.1 mmole) of p-dibromobenzene, 0.14 g of palladium acetate and 0.33 g of 1,1′-bisdiphenyl phosphinoferrocene, 3.46 g of (36.0 mmole) sodium t-butoxide and 43 ml o-xylene were put in a 200 ml three-necked flask, and refluxed under stirring for 15 hours and 30 minutes under argon flow. The reaction mixture was filtered using a filter packed with alumina to remove insoluble matter, the filter was washed with toluene and tetrahydrofuran successively. The filtrate and wash liquid were combined and condensed under reduced pressure. Hexane was added to the residue, followed by heating and stirring, then insoluble matter was removed by filtration, and the filtrate was vacuum dried. Hexane was added to the residue and deposited crystal was filtered off. The filtrate was condensed, and refined by silica gel column chromatography (eluent:hexane/toluene:3/1), recrystallized with hexane to give 3.68 g of a white crystal of 9-(4-bromophenyl)carbazole (yield: 44.4%).

Workup

  1. temperaturerefluxed
  2. filtrationThe reaction mixture was filtered
  3. customto remove insoluble matter
  4. washthe filter was washed with toluene and tetrahydrofuran successively
  5. washThe filtrate and wash liquid
  6. customcondensed under reduced pressure
  7. temperatureby heating
  8. stirringstirring
  9. custominsoluble matter was removed by filtration
  10. customdried
  11. additionHexane was added to the residue
  12. filtrationwas filtered off
  13. customcondensed
  14. customrecrystallized with hexane

Sources & evidence

ORD record
ord-f3a67d2c03fe445e82d6b1bd6d479240
Source dataset
uspto-grants-2009_10
Patent number
US07597955B2

Reaction notes

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