Reaction #1726665

Reaction equation

potassium carbonate

9-iodo-10-phenylanthracene

p-bromophenyl boronic acid

→

light-brown solid

Yield 52.0%

9-(4-bromophenyl)-10-phenylanthracene

Yield 52.0%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   OtherInto a 50 mL three-neck flask were put
2. 2
   OtherThis 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
   WashThe obtained filtrate was washed with water
5. 5
   Dryinga saturated saline, and then dried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationthe obtained filtrate was concentrated
8. 8
   Otherto give a solid
9. 9
   OtherThe obtained solid was recrystallized with chloroform/hexane

Procedure

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%.

Source