反応 #531844

反応方程式

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

収率 85.0%

溶媒

1,2-dimethoxyethane

反応条件

後処理

1. 1
   その他Into a 200 mL three-neck flask were put
2. 2
   その他After the reaction
3. 3
   ろ過a precipitated solid was collected by suction filtration
4. 4
   workup.DISSOLUTIONdissolved in toluene
5. 5
   ろ過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
   洗浄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
   その他was removed
9. 9
   ろ過This suspending solution was naturally filtered
10. 10
    濃縮the obtained filtrate was concentrated
11. 11
    その他the object of the synthesis
12. 12
    その他was obtained in a yield of 85% (synthesis scheme (a-1))

実験手順

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)).

出典