Reaction #531844

Reaction equation

9-bromoanthracene

phenylboronic acid

potassium carbonate

tris(o-tolyl)phosphine

→

9-phenylanthracene

Yield 85.0%

Solvents

1,2-dimethoxyethane

Conditions

Workup

1. 1
   OtherInto a 200 mL three-neck flask were put
2. 2
   OtherAfter the reaction
3. 3
   Filtrationa precipitated solid was collected by suction filtration
4. 4
   workup.DISSOLUTIONdissolved in toluene
5. 5
   Filtrationfiltered 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
   WashThe obtained filtrate was washed with water and saturated aqueous solution and magnesium sulfate
7. 7
   workup.ADDITIONwas added so that the moisture
8. 8
   Otherwas removed
9. 9
   FiltrationThis suspending solution was naturally filtered
10. 10
    Concentrationthe obtained filtrate was concentrated
11. 11
    Otherthe object of the synthesis
12. 12
    Otherwas obtained in a yield of 85% (synthesis scheme (a-1))

Procedure

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)).

Source