Reaktion #1726661

Reaktionsgleichung

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

white powder

Ausbeute 92.0%

9-phenylanthracene

Ausbeute 92.0%

Lösungsmittel

1,2-dimethoxyethane

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture was degassed
2. 2
   workup.STIRRINGstirred under a nitrogen stream at 80° C. for 3 hours
3. 3
   Extraktionan aqueous layer was extracted with toluene
4. 4
   ExtraktionThe obtained extracted solution
5. 5
   Waschenwashed with saturated saline
6. 6
   Trocknenthe organic layer was dried with magnesium sulfate
7. 7
   FiltrationThe obtained 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
8. 8
   Einengenthe filtrate was concentrated
9. 9
   Sonstigeto give a solid
10. 10
    SonstigeThe obtained solid was recrystallized with toluene/methanol

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 1,2-dimethoxyethane (DME), and 25 mL of a 2.0 M potassium carbonate aqueous solution were added. The mixture was degassed by being stirred under reduced pressure, and the atmosphere 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 a nitrogen stream at 80° C. for 3 hours. After a predetermined time, 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 obtained 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 concentrated to give a solid. The obtained solid was recrystallized with toluene/methanol to give 5.8 g of white powder, which was the object of the synthesis, in a yield of 92%.

Quelle