4,4'-Dibromobiphenyl → HCID 22944353, compound

HRID 1445297Notes

Reaction equation

HRID 1445297 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.C[C:18]([CH3:21])([O-])[CH3:19].[Na+].C(P([C:32]([CH3:35])([CH3:34])C)C(C)(C)C)(C)(C)C.Br[C:37]1[CH:42]=[CH:41][C:40]([C:43]2[CH:48]=[CH:47][C:46](Br)=[CH:45][CH:44]=2)=[CH:39][CH:38]=1>CC1C=CC(C)=CC=1.[Pd].[Pd].C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1>[C:4]1([N:7]([C:8]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[C:37]2[CH:42]=[CH:41][C:40]([C:43]3[CH:48]=[CH:47][C:46]([N:7]([C:19]4[CH:18]=[CH:21][CH:34]=[CH:32][CH:35]=4)[C:8]4[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=4)=[CH:45][CH:44]=3)=[CH:39][CH:38]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1

Participants

7

Reactant 4

HCID 71104,4'-DibromobiphenylHCID 132714-NitrodiphenylamineHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxide

Product 1

HCID 22944353HCID 22944353, compound

Reagents, catalysts & solvents 2

HCID 9832798Tris(dibenzylideneacetone) dipalladiumCatalystHCID 7809P-XyleneSolvent

Procedure

In a 100 mL three-necked flask were dissolved 1.56 g of 4,4′-dibromobiphenyl, 2.30 g of 4-nitrodiphenylamine, 1.44 g of sodium tert-butoxide and 0.51 g of tris(dibenzylideneacetone) dipalladium in 50 mL of p-xylene, followed by adding 0.3 mL of tri-t-butylphosphine to the resultant mixture, causing a reaction to take place under a nitrogen atmosphere at about 150° C. for about 16 hours. After the reaction was completed, a resultant solution was filtered to remove solid matter, and dissolved in excess chloroform. The salt was filtered using distilled water and the resultant solution was then concentrated. Then, purification was performed through column chromatography and recrystallization, acquiring 1.2 g of N,N′-diphenyl-N,N′-bis(4-nitrophenyl)-1,1-biphenyl-4,4′-diamine in the form of powder. The acquired powder was dissolved in 50 mL ethanol, 1.5 mL hydrazine monohydrate was added thereto with a catalytic amount of 10% Pd/C, followed by refluxing for 24 hours, yielding 0.9 g of N,N′-diphenyl-N,N′-bis(4-aminophenyl)-1,1-biphenyl-4,4′-diamine.

Workup

  1. customa reaction
  2. customat about 150° C.
  3. customfor about 16 hours
  4. filtrationa resultant solution was filtered
  5. customto remove solid matter
  6. dissolutiondissolved in excess chloroform
  7. filtrationThe salt was filtered
  8. distillationusing distilled water
  9. concentrationthe resultant solution was then concentrated
  10. customThen, purification
  11. customwas performed through column chromatography and recrystallization
  12. dissolutionThe acquired powder was dissolved in 50 mL ethanol
  13. addition1.5 mL hydrazine monohydrate was added
  14. temperatureby refluxing for 24 hours

Sources & evidence

ORD record
ord-0c0d1685bc0c4c538e3b91a460f96fc0
Source dataset
uspto-grants-2010_02
Patent number
US07666525B2

Reaction notes

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