4,4'-Dibromobiphenyl → Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine

HRID 1021179Notes

Reaction equation

HRID 1021179 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.[Br:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=2)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:17]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:19][C:14]([N:13]([C:36]2[CH:35]=[CH:34][C:33]([C:30]3[CH:29]=[CH:28][C:27]([Br:26])=[CH:32][CH:31]=3)=[CH:38][CH:37]=2)[C:10]2[CH:11]=[CH:12][C:7]([C:4]3[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=3)=[CH:8][CH:9]=2)=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 71104,4'-DibromobiphenylHCID 11776TriphenylphosphineHCID 504244Bis-biphenyl-4-yl-amineHCID 23676156Sodium t-butoxide

Product 1

HCID 58672377Bisbiphenyl-4-yl-(4'-broMo-biphenyl-4-yl)-aMine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

4,4′-Iminobis(biphenyl) (2.0 g, 6.23 mmol), and 4,4′-dibromobiphenyl (3.9 g, 12.6 mmol) were mixed in 150 mL of anhydrous toluene. To the solution was bubbled nitrogen while stirring for 15 min. Pd(OAc)2 (0.02 g, 0.089 mmol), triphenylphosphine (0.09 g, 0.34 mmol) and tBuONa (1.15 g, 11.9 mmol) were added in sequence. The mixture was heated to reflux overnight under nitrogen. After cooling, the reaction mixture was filtered through Celite pad and the solvent was then evaporated. The residue (3.1 g, 90%) was recrystallized by toluene and the crystal was further purified by boiling with 15 ml degassed toluene, 2.7 g (78%) of the desired compound was collected.

Workup

  1. customTo the solution was bubbled nitrogen
  2. temperatureThe mixture was heated
  3. temperatureto reflux overnight under nitrogen
  4. temperatureAfter cooling
  5. filtrationthe reaction mixture was filtered through Celite pad
  6. customthe solvent was then evaporated
  7. customThe residue (3.1 g, 90%) was recrystallized by toluene
  8. customthe crystal was further purified
  9. customdegassed toluene, 2.7 g (78%) of the desired compound
  10. customwas collected

Sources & evidence

ORD record
ord-23009e21ce1e4bcfa876bd5d526b11cb
Source dataset
uspto-grants-2014_05
Patent number
US08716484B1

Reaction notes

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