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4-Bromobiphenyl → HCID 86762384, compound

HRID 1021171
Notes
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Reaction equation

HRID 1021171 reaction equation
C1(P(C2CCCCC2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[C:19](OC)=[CH:18][CH:17]=[CH:16][C:15]=2OC)CCCCC1.[C:30]1([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)[C:37]=2[NH2:48])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.BrC1C=CC(C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>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]>[C:14]1([C:9]2[CH:8]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:17]([NH:48][C:37]2[C:38]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:39][CH:40]=[CH:41][C:36]=2[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)=[CH:18][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 71014-BromobiphenylHCID 110102262,6-DiphenylanilineHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxide

Product 1

HCID 86762384HCID 86762384, compoundYield 471.7%

Reagents, catalysts & solvents 1

HCID 9811564
Bis(dibenzylideneacetone)palladium
Catalyst

Procedure

Xylene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (4.6 g, 11.2 mmol) and Pd2(dba)3 (2.6 g, 2.8 mmol). The mixture was bubbled with nitrogen for 15 min, then [1,1′:3′,1″-terphenyl]-2′-amine (13.7 g, 56.0 mmol), 4-bromobiphenyl (13.0 g, 56.0 mmol), sodium tert-butoxide (10.8 g, 112.0 mmol) were added. The mixture was bubbled with nitrogen for 15 min and refluxed for 12 h. After cooling, the reaction mixture was filtered through a silica pad and washed with toluene. The solvent was removed in vacuo and the residue was purified by flash chromatography using 30-40% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-[1,1′:3′,1″-terphenyl]-2′-amine (21.0 g, 93% yield) as a white solid.

Workup

  1. customXylene (250 mL) was bubbled with nitrogen for 15 min
  2. customThe mixture was bubbled with nitrogen for 15 min
  3. customThe mixture was bubbled with nitrogen for 15 min
  4. temperaturerefluxed for 12 h
  5. temperatureAfter cooling
  6. filtrationthe reaction mixture was filtered through a silica pad
  7. washwashed with toluene
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-359e52bcfd01480f961ed9816339ce3e
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08716484B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes