반응 #1726661

반응 방정식

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

white powder

수율 92.0%

9-phenylanthracene

수율 92.0%

용매

1,2-dimethoxyethane

water

반응 조건

후처리

1. 1
   기타The mixture was degassed
2. 2
   workup.STIRRINGstirred under a nitrogen stream at 80° C. for 3 hours
3. 3
   추출an aqueous layer was extracted with toluene
4. 4
   추출The obtained extracted solution
5. 5
   세척washed with saturated saline
6. 6
   건조the organic layer was dried with magnesium sulfate
7. 7
   여과The 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
   농축the filtrate was concentrated
9. 9
   기타to give a solid
10. 10
    기타The obtained solid was recrystallized with toluene/methanol

실험 절차

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%.

출처