Carbazole → 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole

HRID 403151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 403151
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Br[C:15]1[CH:16]=[C:17]([Si:21]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([Br:40])[CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:18]=[CH:19][CH:20]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[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]>[Br:40][C:36]1[CH:35]=[C:34]([Si:21]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)([C:17]2[CH:16]=[CH:15][CH:20]=[CH:19][CH:18]=2)[C:22]2[CH:23]=[C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=4[C:5]4[C:13]3=[CH:1][CH:2]=[CH:3][CH:4]=4)[CH:25]=[CH:26][CH:27]=2)[CH:39]=[CH:38][CH:37]=1

Komponenten

7

Edukt 3

HCID 6854CarbazoleHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 866740529-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazoleAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)KatalysatorHCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

A suspension of 9H-carbazole (3.60 g, 21.53 mmol), bis(3-bromophenyl)diphenylsilane (21.28 g, 43.1 mmol), Pd2(dba)3 (0.394 g, 0.431 mmol), 1,1′-Bis(diphenylphosphino)ferrocene (dppf, 0.394 g, 0.431 mmol) and sodium tert-butoxide (4.14 g, 43.1 mmol) in xylene (150 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic solution was isolated by filtration. Upon evaporation of the solvent, the crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1, v/v) as eluent to yield 9-(3-((3-bromophenyl)diphenylsilyl)phenyl)-9H-carbazole (6.1 g, 49%) as white solid

Aufarbeitung

  1. temperaturewas refluxed under nitrogen overnight
  2. customthe organic solution was isolated by filtration
  3. customUpon evaporation of the solvent
  4. customthe crude product was purified by column chromatography on silica gel with hexane:EtOAc (9:1

Quellen und Nachweise

ORD-Eintrag
ord-17f25f041a3a45359fb9f21bee359959
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748012B2

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