Reaktion #624773

Reaktionsgleichung

9-bromoanthracene

potassium carbonate

tris(ortho-tolyl)phosphine

phenylboronic acid

→

9-phenylanthracene

Ausbeute 85.0%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter reaction
2. 2
   Filtrationa precipitated solid was collected by suction filtration
3. 3
   workup.DISSOLUTIONSubsequently, the solid was dissolved in toluene
4. 4
   Filtrationfiltered through florisil, celite, and alumina
5. 5
   WaschenAfter a filtrate was washed with water and saturated saline, it
6. 6
   Trocknenwas dried with magnesium sulfate
7. 7
   FiltrationAfter the mixture was subjected to natural filtration, when the filtrate
8. 8
   Einengenwas concentrated
9. 9
   Sonstigewas obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1))

Vorschrift

5.4 g (21.1 mmol) of 9-bromoanthracene, 2.6 g (21.1 mmol) of phenylboronic acid, 60 mg (0.21 mmol) of palladium(II) acetate (abbreviation: Pd(OAc)2), 10 mL (20 mmol) of a potassium carbonate aqueous solution (2 mol/L), 263 mg (0.84 mmol) of tris(ortho-tolyl)phosphine (abbreviation: P(o-tolyl)3), and 20 mL of 1,2-dimethoxyethane (abbreviation: DME) were put in a 200 mL three neck flask, and then stirred for nine hours at 80° C. in nitrogen stream. After reaction, a precipitated solid was collected by suction filtration. Subsequently, the solid was dissolved in toluene and then filtered through florisil, celite, and alumina. After a filtrate was washed with water and saturated saline, it was dried with magnesium sulfate. After the mixture was subjected to natural filtration, when the filtrate was concentrated, 21.5 g of 9-phenylanthracene which was a target substance was obtained as a light brown solid at a yield of 85% (Synthesis scheme (b-1)).

Quelle