Potassium Phosphate, Tribasic → 3,3'-Bicarbazole

HRID 1957901Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1957901
Br[C:2]1[CH:3]=[CH:4][C:5]2[NH:6][C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C1([N:21]2[C:33]3[CH:32]=[CH:31][C:30](B4OC(C)(C)C(C)(C)O4)=[CH:29][C:28]=3[C:27]3[C:22]2=[CH:23][CH:24]=[CH:25][CH:26]=3)C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.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].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>[CH:4]1[C:5]2[NH:6][C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]=2[CH:14]=[C:2]([C:25]2[CH:24]=[CH:23][C:22]3[NH:21][C:33]4[C:28]([C:27]=3[CH:26]=2)=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:3]=1

Komponenten

8

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 2524463-BromocarbazoleHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole

Produkt 1

HCID 124626013,3'-BicarbazoleAusbeute 73,1 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture solution of 3-bromo-9H-carbazole (6.75 g, 27.4 mmol), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (12.15 g, 32.9 mmol), Pd2(dba)3 (0.251 g, 0.274 mmol), SPhos (0.450 g, 1.097 mmol) and K3PO4 (25.3 g, 110 mmol) in toluene (500 mL) and water (50 mL) was refluxed under nitrogen for 10 h. After cooling to room temperature, the reaction mixture was extracted with dichloromethane and washed with brine. The combined organic solutions were dried over Na2SO4, filtered, and the solvent was evaporated to yield a crude product, which was recrystallized from DCM/hexane (1/1, v/v, 1200 mL) to yield 9H,9′H-3,3′-bicarbazole (6.66 g, 59%) as a yellow solid.

Aufarbeitung

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washwashed with brine
  3. dry with materialThe combined organic solutions were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customto yield a crude product, which
  7. customwas recrystallized from DCM/hexane (1/1, v/v, 1200 mL)

Quellen und Nachweise

ORD-Eintrag
ord-c7513b90ab5c4dafa0b5b61a4b7432b3
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08409729B2

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