Reaktion #1726665

Reaktionsgleichung

potassium carbonate

9-iodo-10-phenylanthracene

p-bromophenyl boronic acid

→

light-brown solid

Ausbeute 52.0%

9-(4-bromophenyl)-10-phenylanthracene

Ausbeute 52.0%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeInto a 50 mL three-neck flask were put
2. 2
   SonstigeThis mixture was degassed under reduced pressure
3. 3
   FiltrationThen, the mixture was subjected to suction filtration 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
4. 4
   WaschenThe obtained filtrate was washed with water
5. 5
   Trocknena saturated saline, and then dried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenthe obtained filtrate was concentrated
8. 8
   Sonstigeto give a solid
9. 9
   SonstigeThe obtained solid was recrystallized with chloroform/hexane

Vorschrift

Into a 50 mL three-neck flask were put 1.0 g (2.63 mmol) of 9-iodo-10-phenylanthracene and 542 mg (2.70 mmol) of p-bromophenyl boronic acid. The atmosphere in the flask was replaced with nitrogen. After that, 10 mL of toluene and 3 mL of potassium carbonate aqueous solution (2.0 M) were added to the flask. This mixture was degassed under reduced pressure, then 46 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. The mixture was stirred under a nitrogen stream at 80° C. for 9 hours. After the stirring, about 20 mL of toluene was added to this mixture. Then, the mixture was subjected to suction filtration 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 a saturated saline, and then dried with magnesium sulfate. This mixture was gravity filtered, and the obtained filtrate was concentrated to give a solid. The obtained solid was recrystallized with chloroform/hexane to give 0.56 g of a light-brown solid, which was the object of the synthesis, in a yield of 45%.

Quelle