反应 #1726661

反应方程式

9-bromoanthracene

phenylboronic acid

tri(ortho-tolyl)phosphine

potassium carbonate

→

white powder

收率 92.0%

9-phenylanthracene

收率 92.0%

溶剂

1,2-dimethoxyethane

water

反应条件

后处理

1. 1
   其他The mixture was degassed
2. 2
   workup.STIRRINGstirred under a nitrogen stream at 80° C. for 3 hours
3. 3
   萃取an aqueous layer was extracted with toluene
4. 4
   萃取The obtained extracted solution
5. 5
   洗涤washed with saturated saline
6. 6
   干燥the organic layer was dried with magnesium sulfate
7. 7
   过滤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
   浓缩the filtrate was concentrated
9. 9
   其他to give a solid
10. 10
    其他The obtained solid was recrystallized with toluene/methanol

实验过程

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%.

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