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1-Bromo-4-iodobenzene → N,N-bis(4-bromophenyl)-N',N'-dipheny-1,4-phenylenediamine

HRID 1873937
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1873937
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[CH:9]1[CH:14]=[CH:13][C:12]([N:15]([C:22]2[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:11][CH:10]=1.C[C:30]([CH3:33])([O-])[CH3:31].[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.[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].C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:28]([C:31]2[CH:30]=[CH:33][C:2]([Br:1])=[CH:3][CH:4]=2)[C:25]2[CH:26]=[CH:27][C:22]([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]3[CH:11]=[CH:10][CH:9]=[CH:14][CH:13]=3)=[CH:23][CH:24]=2)=[CH:4][CH:3]=1
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Komponenten

7

Edukt 3

HCID 115221-Bromo-4-iodobenzeneHCID 75371N,N-Diphenyl-p-phenylenediamineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 22605056N,N-bis(4-bromophenyl)-N',N'-dipheny-1,4-phenylenediamineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)
Katalysator
HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

First, 27.2 mmol of 1-bromo-4-iodobenzene, 13.6 mmol of 4-Amino triphenylamine, 0.27 mmol of bis(dibenzylideneacetone)palladium ([Pd(dba)2]), 0.54 mmol of 1,1′-bis(diphenylphosphino)ferrocene (DPPF), 40.8 mmol of sodium tert-butoxide and 18 ml toluene were added into a 250 ml bottle. After heating to reflux under a nitrogen atmosphere for 6 hrs, the solvent was removed under reduced pressure, and the residue was extracted with dichloromethane/water. The collected organic layer was dried by MgSO4 overnight and then filtered to remove MgSO4. After removing the solvent of filtrate, the residue was purified by silica gel column chromatography (dichloromethane:n-hexane=1:3) and recrystallized from hexane to obtain N,N-bis(4-bromophenyl)-N′,N′-dipheny-1,4-phenylenediamine (DTPADBR) as white crystals (61% yield).

Aufarbeitung

  1. temperatureAfter heating
  2. temperatureto reflux under a nitrogen atmosphere for 6 hrs
  3. customthe solvent was removed under reduced pressure
  4. extractionthe residue was extracted with dichloromethane/water
  5. dry with materialThe collected organic layer was dried by MgSO4 overnight
  6. filtrationfiltered
  7. customto remove MgSO4
  8. customAfter removing the solvent of filtrate
  9. customthe residue was purified by silica gel column chromatography (dichloromethane:n-hexane=1:3)
  10. customrecrystallized from hexane

Quellen und Nachweise

ORD-Eintrag
ord-65a0fd4a93674b8983961bcc0f2b9c26
Quelldatensatz
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08304514B2

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