Réaction #1726661

Équation de réaction

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

white powder

Rendement 92.0%

9-phenylanthracene

Rendement 92.0%

Solvants

1,2-dimethoxyethane

water

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was degassed
2. 2
   workup.STIRRINGstirred under a nitrogen stream at 80° C. for 3 hours
3. 3
   Extractionan aqueous layer was extracted with toluene
4. 4
   ExtractionThe obtained extracted solution
5. 5
   Lavagewashed with saturated saline
6. 6
   Séchagethe 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
   Concentrationthe filtrate was concentrated
9. 9
   Autreto give a solid
10. 10
    AutreThe obtained solid was recrystallized with toluene/methanol

Mode opératoire

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%.

Source