Reaktion #633831

Reaktionsgleichung

potassium carbonate

9-bromoanthracene

phenylboronic acid

→

9-phenylanthracene

Ausbeute 82.0%

Lösungsmittel

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeto be reacted
2. 2
   SonstigeAfter the reaction
3. 3
   Filtrationa precipitate in the reaction mixture was collected by suction filtration
4. 4
   SonstigeThe obtained solid was recrystallized by a mixed solvent of chloroform and hexane

Vorschrift

25.4 g (100 mmol) of 9-bromoanthracene, 12.8 g (105 mmol) of phenylboronic acid, 0.233 g (1.00 mmol) of palladium (II) acetate, and 0.913 g (3.00 mmol) of tri(ortho-tolyl)phosphine were put into a 500 mL three-necked flask. Then, the atmosphere in the flask was substituted with nitrogen. Thereafter, 100 mL of ethylene glycol dimethyl ether (abbreviation: DME) and 75 mL (150 mmol) of potassium carbonate solution (2.0 mol/L) were added to the mixture, and this mixture was refluxed at 90° C. for 6 hours to be reacted. After the reaction, a precipitate in the reaction mixture was collected by suction filtration. The obtained solid was recrystallized by a mixed solvent of chloroform and hexane; then 20.8 g of objective 9-phenylanthracene was obtained as a white powdered solid in a yield of 82%. A synthetic scheme of 9-phenylanthracene is illustrated below (synthetic scheme b-1).

Quelle