Reaction #1747846

Reaction equation

9-phenanthreneboronic acid

4-bromoiodobenzene

sodium carbonate

→

9-(4-bromophenyl)phenanthrene

Yield 72.0%

Solvents

toluene

Conditions

Workup

1. 1
   Temperaturewhile being refluxed
2. 2
   OtherAfter the reaction in the mixture
3. 3
   Filtrationfiltration
4. 4
   Dryingdried with magnesium sulfate, toluene
5. 5
   workup.DISTILLATIONwas distilled away under reduced pressure
6. 6
   Otherwas obtained with an yield of 72%

Procedure

Under an argon gas atmosphere, 39.25 g (177 mmol) of 9-phenanthreneboronic acid, 50.0 g (177 mmol) of 4-bromoiodobenzene, 4.10 g (3.54 mmol) of tetrakis(triphenylphosphine) palladium(0), 400 mL of toluene and 265 mL of 2M sodium carbonate solution were mixed, and stirred for 24 hours while being refluxed. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 42.6 g of 9-(4-bromophenyl)phenanthrene was obtained with an yield of 72%.

Source