4,4'-Dibromobiphenyl → HCID 86762389, Verbindung

HRID 1021176Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1021176
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]1([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:25]=[CH:24][C:23]([NH:26][C:27]2[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH:21]=1.[Br:45][C:46]1[CH:51]=[CH:50][C:49]([C:52]2[CH:57]=[CH:56][C:55](Br)=[CH:54][CH:53]=2)=[CH:48][CH:47]=1.CC(C)([O-])C.[Na+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:20]1([C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:25]=[CH:24][C:23]([N:26]([C:55]2[CH:54]=[CH:53][C:52]([C:49]3[CH:48]=[CH:47][C:46]([Br:45])=[CH:51][CH:50]=3)=[CH:57][CH:56]=2)[C:27]2[C:28]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 71104,4'-DibromobiphenylHCID 11776TriphenylphosphineHCID 23676156Sodium t-butoxideHCID 86762387Biphenyl-4-yl-biphenyl-2-yl-amin

Produkt 1

HCID 86762389HCID 86762389, VerbindungAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 167845palladium(II) acetateKatalysator

Versuchsvorschrift

Toluene (250 mL) was bubbled with nitrogen for 15 min, followed by addition of triphenylphosphine (0.2 g, 0.8 mmol) and Pd(OAc)2 (0.05 g, 0.2 mmol). The mixture was bubbled with nitrogen for 15 min, then N-([1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (3.4 g, 10.5 mmol), 4,4′-dibromobiphenyl (6.6 g, 21.0 mmol), sodium tert-butoxide (2.0 g, 21.0 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 20% toluene/hexane to afford N-([1,1′-biphenyl]-4-yl)-N-(4′-bromo-[1,1′-biphenyl]-4-yl)-[1,1′-biphenyl]-2-amine (4.2 g, 73% yield) as a white solid.

Aufarbeitung

  1. customToluene (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

Quellen und Nachweise

ORD-Eintrag
ord-833970d2a5234159b2d01676fe74dfa8
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716484B1

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