Reaktion #92823

Reaktionsgleichung

3-bromocarbazole

dibenzothiophene-4-boronic acid

potassium carbonate

tri(ortho-tolyl)phosphine

→

3-(Dibenzothiophen-4-yl)-9H-carbazole

Ausbeute 32.0%

Lösungsmittel

ethanol

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 200-mL three-neck flask were put
2. 2
   SonstigeIn the flask, the mixture was degassed
3. 3
   TemperaturAfter the reflux, the mixture was cooled to room temperature
4. 4
   Filtrationthe precipitated solid was collected by suction filtration
5. 5
   workup.DISSOLUTIONThe collected solid was dissolved in 100 mL of toluene
6. 6
   Filtrationthis solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina
7. 7
   SonstigeThe solid obtained by concentration of the obtained filtrate
8. 8
   Sonstigewas recrystallized from toluene/hexane, so that 1.4 g of a white solid, which
9. 9
   Sonstigethe object of the synthesis
10. 10
    Sonstigewas obtained in 32% yield
11. 11
    SonstigeThe synthesis scheme of Step 1

Vorschrift

In a 200-mL three-neck flask were put 3.0 g (12 mmol) of 3-bromocarbazole, 2.8 g (12 mmol) of dibenzothiophene-4-boronic acid, and 150 mg (0.5 mol) of tri(ortho-tolyl)phosphine, and the air in the flask was replaced with nitrogen. To this mixture were added 40 mL of toluene, 40 mL of ethanol, and 15 mL (2.0 mol/L) of an aqueous potassium carbonate solution. In the flask, the mixture was degassed by being stirred under reduced pressure. After the degassing, replacement with nitrogen was performed, and 23 mg (0.10 mmol) of palladium(II) acetate was added to this mixture, and then the mixture was refluxed at 110° C. for 3 hours. After the reflux, the mixture was cooled to room temperature, and then the precipitated solid was collected by suction filtration. The collected solid was dissolved in 100 mL of toluene, and this solution was filtered through Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), and alumina. The solid obtained by concentration of the obtained filtrate was recrystallized from toluene/hexane, so that 1.4 g of a white solid, which was the object of the synthesis, was obtained in 32% yield. The synthesis scheme of Step 1 is illustrated in (a-1).

Quelle