1,4-Dibromobenzene → HCID 86762388, compound

HRID 1021175Notes

Reaction equation

HRID 1021175 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30](Br)=[CH:29][CH:28]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]1([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:6]=[CH:5][C:4]([N:7]([C:30]2[CH:31]=[CH:32][C:27]([Br:26])=[CH:28][CH:29]=2)[C:8]2[C:9]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 23676156Sodium t-butoxideHCID 86762387Biphenyl-4-yl- biphenyl-2-yl-amin;N-{[1,1'-biphenyl]-4-yl}-[1,1'-biphenyl]-2-amine

Product 1

HCID 86762388HCID 86762388, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalyst

Procedure

Toluene (500 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.4 g, 1.7 mmol) and Pd(OAc)2 (0.10 g, 0.42 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (6.7 g, 21.0 mmol), 1,4-dibromobenzene (14.9 g, 63.0 mmol), sodium tert-butoxide (4.0 g, 42.0 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 (containing 0.5% triethylamine). The solvent was removed in vacuo and the residue was purified by flash chromatography using 10-20% toluene/hexane (containing 0.5% triethylamine) to afford N-([1,1′-biphenyl]-4-yl)-N-(4-bromophenyl)-[1,1′-biphenyl]-2-amine (8.7 g, 87% yield) as a white solid.

Workup

  1. customToluene (500 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 (containing 0.5% triethylamine)
  8. customThe solvent was removed in vacuo
  9. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fd0095f01a244f86af9fc3ad4e05623c
Source dataset
uspto-grants-2014_05
Patent number
US08716484B1

Reaction notes

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