Carbazole → 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole

HRID 403151Notes

Reaction equation

HRID 403151 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:16]=[C:17]([Si:21]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Br:40])[CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Br:40][C:36]1[CH:35]=[C:34]([Si:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:17]2[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=2)[C:22]2[CH:23]=[C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH:25]=[CH:26][CH:27]=2)[CH:39]=[CH:38][CH:37]=1

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 23676156Sodium t-butoxide

Product 1

HCID 866740529-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazoleYield 49%

Reagents, catalysts & solvents 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 7237O-XyleneSolvent

Procedure

A suspension of 9H-carbazole (3.60 g, 21.53 mmol), bis(3-bromophenyl)diphenylsilane (21.28 g, 43.1 mmol), Pd2(dba)3 (0.394 g, 0.431 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (dppf, 0.394 g, 0.431 mmol) and sodium tert-butoxide (4.14 g, 43.1 mmol) in xylene (150 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic solution was isolated by filtration. Upon evaporation of the solvent, the crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1, v/v) as eluent to yield 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole (6.1 g, 49%) as white solid

Workup

  1. temperaturewas refluxed under nitrogen overnight
  2. customthe organic solution was isolated by filtration
  3. customUpon evaporation of the solvent
  4. customthe crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1

Sources & evidence

ORD record
ord-17f25f041a3a45359fb9f21bee359959
Source dataset
uspto-grants-2014_06
Patent number
US08748012B2

Reaction notes

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