反応 #1726661

反応方程式

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

white powder

収率 92.0%

9-phenylanthracene

収率 92.0%

溶媒

1,2-dimethoxyethane

water

反応条件

後処理

1. 1
   その他The mixture was degassed
2. 2
   workup.STIRRINGstirred under a nitrogen stream at 80° C. for 3 hours
3. 3
   抽出an aqueous layer was extracted with toluene
4. 4
   抽出The obtained extracted solution
5. 5
   洗浄washed with saturated saline
6. 6
   乾燥the organic layer was dried with magnesium sulfate
7. 7
   ろ過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
8. 8
   濃縮the filtrate was concentrated
9. 9
   その他to give a solid
10. 10
    その他The obtained solid was recrystallized with toluene/methanol

実験手順

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%.

出典