Iodobenzene → 2-Bromo-9-phenyl-9H-carbazole

HRID 1473733Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1473733
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:12][C:11]=2[CH:10]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1(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]>[Br:8][C:9]1[CH:21]=[CH:20][C:19]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:11]=2[CH:10]=1

Komponenten

7

Edukt 4

HCID 11575IodobenzeneHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 127170892-Bromo-9H-carbazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 668380442-Bromo-9-phenyl-9H-carbazoleAusbeute 37,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

30.51 g (149.56 mmol) of iodobenzene, 18.32 g (74.78 mmol) of 2-bromo-9H-carbazole, 14.37 g (149.56 mmol) of sodium t-butoxide, and 1.81 ml (7.48 mmol) of tritertbutylphosphine were dissolved in 300 ml of toluene, and 0.68 g (0.75 mmol) of Pd2(dba)3 was added thereto, and refluxed and agitated for 12 hours. After the reaction was finished, extraction was performed by dichloromethane, filtering was performed by silica gel, and the column was used at a ratio of hexane:MC=9:1 (v/v) to obtain 8.99 g of 2-bromo-9-phenylcarbazole (yield 37%).

Aufarbeitung

  1. temperaturerefluxed
  2. extractionextraction
  3. filtrationfiltering

Quellen und Nachweise

ORD-Eintrag
ord-42b2fd1ef53a45db89acabe54edde7d6
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09017829B2

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