Reaction #1726663

Reaction equation

sodium carbonate

9-iodo-10-phenylanthracene

4′-bromobiphenyl-4-boronic acid

→

light yellow powdered solid

Yield 40.1%

9-(4′-bromobiphenyl-4-yl)-10-phenylanthracene

Yield 40.1%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   OtherInto a 100 mL three-neck flask were put
2. 2
   Otherto be degassed
3. 3
   workup.STIRRINGThe mixture was stirred at 90° C. for 4 hours
4. 4
   FiltrationThe mixture was subjected to suction filtration through alumina, Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135)
5. 5
   OtherThe solid obtained by condensation of the obtained filtrate
6. 6
   Otherwas purified by high-performance liquid chromatography (the mobile phase
7. 7
   Otherchloroform) to give a light yellow solid
8. 8
   OtherThe obtained solid was recrystallized with chloroform/hexane

Procedure

Into a 100 mL three-neck flask were put 2.8 g (7.2 mmol) of 9-iodo-10-phenylanthracene and 1.5 g (7.2 mmol) of 4′-bromobiphenyl-4-boronic acid, and the atmosphere in the flask was replaced with nitrogen. To the mixture, 40 mL of toluene and 10 mL (2.0 mol/L) of a sodium carbonate aqueous solution were added. The mixture was stirred under reduced pressure to be degassed. After the degassing, 120 mg (0.10 mmol) of tetrakis(triphenylphosphine)palladium(0) was added to the mixture. The mixture was stirred at 90° C. for 4 hours. After the stirring, about 50 mL of toluene was added to the mixture. The mixture was subjected to suction filtration through alumina, Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135). The solid obtained by condensation of the obtained filtrate was purified by high-performance liquid chromatography (the mobile phase: chloroform) to give a light yellow solid. The obtained solid was recrystallized with chloroform/hexane to give 1.4 g of a light yellow powdered solid, which was the object of the synthesis, in a yield of 40%.

Source