Reaktion #622416

Reaktionsgleichung

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

9-phenylanthracene

Lösungsmittel

ethylene glycol dimethyl ether

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   workup.STIRRINGstirred under nitrogen stream at 80° C. for 3 hours
3. 3
   workup.WAITAfter a certain period
4. 4
   Extraktionan aqueous layer was extracted with toluene
5. 5
   ExtraktionThe obtained extracted solution
6. 6
   Waschenwashed with saturated saline
7. 7
   Trocknenthe organic layer was dried with magnesium sulfate
8. 8
   FiltrationThe mixture was subjected to suction filtration 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
9. 9
   Sonstigecondensed
10. 10
    Sonstigeto give a solid
11. 11
    SonstigeThe solid was recrystallized with toluene/methonol, so that 5.8 g of target white powder
12. 12
    Sonstigewas obtained in a yield of 92%

Vorschrift

In a 200 mL three-neck flask, 6.4 g (25 mmol) of 9-bromoanthracene, 3.0 g (25 mmol) of phenylboronic acid, 0.76 g (2.5 mmol) of tri(ortho-tolyl)phosphine, 60 mL of ethylene glycol dimethyl ether (DME), and 25 mL of a 2.0 M potassium carbonate solution were placed. The mixture was degassed by being stirred under reduced pressure, and the air in the flask was replaced with nitrogen. To the mixture, 0.11 g (0.50 mmol) of palladium(II) acetate was added and stirred under nitrogen stream at 80° C. for 3 hours. After a certain period, water was added to the mixture, and an aqueous layer was extracted with toluene. The obtained extracted solution and the organic layer were combined and washed with saturated saline, and the organic layer was dried with magnesium sulfate. The mixture was subjected to suction filtration 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, and the filtrate was condensed to give a solid. The solid was recrystallized with toluene/methonol, so that 5.8 g of target white powder was obtained in a yield of 92%.

Quelle