반응 #531844

반응 방정식

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

수율 85.0%

용매

1,2-dimethoxyethane

반응 조건

후처리

1. 1
   기타Into a 200 mL three-neck flask were put
2. 2
   기타After the reaction
3. 3
   여과a precipitated solid was collected by suction filtration
4. 4
   workup.DISSOLUTIONdissolved in toluene
5. 5
   여과filtered 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
   세척The obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate
7. 7
   workup.ADDITIONwas added so that the moisture
8. 8
   기타was removed
9. 9
   여과This suspending solution was naturally filtered
10. 10
    농축the obtained filtrate was concentrated
11. 11
    기타the object of the synthesis
12. 12
    기타was obtained in a yield of 85% (synthesis scheme (a-1))

실험 절차

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)).

출처