Carbazole → HCID 53889807, Verbindung

HRID 532093

Reaktionsgleichung

Reaktionsgleichung von HRID 532093
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([I:14])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH:15]1[C:27]2[NH:26][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>[Cu]I.O.CN1CCCN(C)C1=O>[I:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2[CH:6]=[CH:7][C:2]([N:26]3[C:27]4[CH:15]=[CH:16][CH:17]=[CH:18][C:19]=4[C:20]4[C:25]3=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:3][CH:4]=2)=[CH:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 763484,4'-Diiodo-1,1'-biphenyl

Produkt 1

HCID 53889807HCID 53889807, VerbindungAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Reaktionsbedingungen

Temperatur
170 °C

Versuchsvorschrift

Initially, 49 g (120 mmol) of diiodobiphenyl, 17 g (100 mmol) of carbazole, 1.0 g (5.0 mmol) of copper(I) iodide, 1.3 g (5.0 mmol) of 18-crown-6-ether, 10 g (75 mmol) of potassium carbonate, 40 mL of 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (abbreviation: DMPU) were put in a 500 mL three-neck flask, and the atmosphere of the flask was substituted by nitrogen. The mixture was stirred at 170° C. for 6.5 hours. After stirring, water was added to the mixture and the mixture was filtrated to give a precipitate. The precipitate was washed with 1M hydrochloric acid, water, an aqueous solution of sodium hydrogen carbonate, and water in this order, and then was recrystallized from a mixture solution of toluene and hexane. The resulting solid was recrystallized from chloroform to give 40 g of the target substance, white powder of 9-(4′-iodobiphenyl-4-yl)-9H-carbazole in a yield of 89%.

Aufarbeitung

  1. stirringAfter stirring
  2. filtrationthe mixture was filtrated
  3. customto give a precipitate
  4. washThe precipitate was washed with 1M hydrochloric acid, water
  5. customan aqueous solution of sodium hydrogen carbonate, and water in this order, and then was recrystallized from a mixture solution of toluene and hexane
  6. customThe resulting solid was recrystallized from chloroform

Quellen und Nachweise

ORD-Eintrag
ord-2f45593c145747d095d7186bc097f9d7
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08852758B2

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