反应 #531844

反应方程式

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

收率 85.0%

溶剂

1,2-dimethoxyethane

反应条件

后处理

1. 1
   其他Into a 200 mL three-neck flask were put
2. 2
   其他After the reaction
3. 3
   过滤a precipitated solid was collected by suction filtration
4. 4
   workup.DISSOLUTIONdissolved in toluene
5. 5
   过滤filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina
6. 6
   洗涤The obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate
7. 7
   workup.ADDITIONwas added so that the moisture
8. 8
   其他was removed
9. 9
   过滤This suspending solution was naturally filtered
10. 10
    浓缩the obtained filtrate was concentrated
11. 11
    其他the object of the synthesis
12. 12
    其他was obtained in a yield of 85% (synthesis scheme (a-1))

实验过程

Into a 200 mL three-neck flask were put 5.4 g (21 mmol) of 9-bromoanthracene, 2.6 g (21 mmol) of phenylboronic acid, 60 mg (0.2 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2), 10 mL (20 mmol) of potassium carbonate aqueous solution (2.0 mol/L), 260 mg (0.8 mmol) of tris(o-tolyl)phosphine (abbreviation: P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME), and then the mixture was stirred at 80° C. in a nitrogen atmosphere for 9 hours. After the reaction, a precipitated solid was collected by suction filtration, dissolved in toluene, and filtered through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate was added so that the moisture was removed. This suspending solution was naturally filtered and the obtained filtrate was concentrated, whereby 22 g of a light-brown solid of 9-phenylanthracene, which was the object of the synthesis, was obtained in a yield of 85% (synthesis scheme (a-1)).

来源