Reacción #531844

Ecuación de reacción

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

Rendimiento 85.0%

Disolventes

1,2-dimethoxyethane

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroInto a 200 mL three-neck flask were put
2. 2
   OtroAfter the reaction
3. 3
   Filtracióna precipitated solid was collected by suction filtration
4. 4
   workup.DISSOLUTIONdissolved in toluene
5. 5
   Filtraciónfiltered 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
   LavadoThe obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate
7. 7
   workup.ADDITIONwas added so that the moisture
8. 8
   Otrowas removed
9. 9
   FiltraciónThis suspending solution was naturally filtered
10. 10
    Concentraciónthe obtained filtrate was concentrated
11. 11
    Otrothe object of the synthesis
12. 12
    Otrowas obtained in a yield of 85% (synthesis scheme (a-1))

Procedimiento

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)).

Fuente