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Carbazole → 9-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazole

HRID 1424767
Notes
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Reaction equation

HRID 1424767 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:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23](Br)[CH:22]=2)[CH:18]=[CH:19][CH:20]=1.CC([O-])(C)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:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([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:26]=2)[CH:18]=[CH:19][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 6854CarbazoleHCID 1539873,3'-DibromobiphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 588711539-(3'-bromo-[1,1'-biphenyl]-3-yl)-9H-carbazoleYield 54.7%

Reagents, catalysts & solvents 3

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

Procedure

9H-carbazole (10 g, 59.8 mmol) and 3,3′-dibromo-1,1′-biphenyl (41.1 g, 132 mmol) were dissolved in xylene (100 ml). Sodium 2-methylpropan-2-olate (8.62 g, 90 mmol), Tris(dibenzylideneacetone)dipalladium(0) (Pd2dba3) (0.548 g, 0.598 mmol) and 1,1′-bis(diphenylphosphanyl) ferrocene (dppf) (0.663 g, 1.196 mmol) were then added into the mixture. The reaction mixture was degassed with nitrogen for 30 minutes, and heated to reflux for 48 h. The crude mixture was filtered through a pad of Celite® and washed with DCM. The solvents were evaporated under vacuum and the material was purified via column chromatography using hexane and DCM (95/5). After the excess of dibromobiphenyl came out, the polarity was increased gradually to 30% DCM in hexane. The compound 9-(3′-bromo-[1,1′-biphenyl]-3-yl)-9H-carbazole (13.02 g, 32.7 mmol, 54.7% yield) was afforded as white solids.

Workup

  1. customThe reaction mixture was degassed with nitrogen for 30 minutes
  2. temperatureheated
  3. temperatureto reflux for 48 h
  4. filtrationThe crude mixture was filtered through a pad of Celite®
  5. washwashed with DCM
  6. customThe solvents were evaporated under vacuum
  7. customthe material was purified via column chromatography
  8. temperaturethe polarity was increased gradually to 30% DCM in hexane

Sources & evidence

ORD record
ord-cabf28ecc2e94ed8bbc28e6a0aceb5ad
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927749B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes