Water → 9-Phenyl-9H,9'H-[3,3']bicarbazolyl

HRID 634556

Reaktionsgleichung

Reaktionsgleichung von HRID 634556
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.C(=O)([O-])[O-].[Na+].[Na+].[C:21]1([CH3:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]1([N:6]2[C:5]3[CH:4]=[CH:3][C:2]([C:2]4[CH:3]=[CH:4][C:5]5[NH:6][C:26]6[C:21]([C:27]=5[CH:14]=4)=[CH:22][CH:23]=[CH:24][CH:25]=6)=[CH:14][C:13]=3[C:12]3[C:7]2=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 1140TolueneHCID 10340Sodium CarbonateHCID 2524463-Bromocarbazole

Produkt 1

HCID 593066299-Phenyl-9H,9'H-[3,3']bicarbazolyl

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

24.10 g (97.92 mmol) of 3-bromo-9H-carbazole 22, 30.93 g (107.71 mmol) of compound 25 and 11.56 g of sodium carbonate are suspended in 2500 ml of dioxane, 2500 ml of toluene and 1000 ml of water. 5.79 g (5.01 mmol) of Pd(PPh3)4 are added to this suspension. The reaction mixture is heated under reflux for 5 h. After cooling, the precipitated solid is filtered off with suction, washed with water and ethanol and dried. The residue is extracted with hot toluene and recrystallised from toluene. The yield is 22.0 g (55%).

Aufarbeitung

  1. temperatureThe reaction mixture is heated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling
  4. filtrationthe precipitated solid is filtered off with suction
  5. washwashed with water and ethanol
  6. customdried
  7. extractionThe residue is extracted with hot toluene
  8. customrecrystallised from toluene

Quellen und Nachweise

ORD-Eintrag
ord-1c4d639f2e6c4048a520ae65408c2072
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09324954B2

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