Reaction #1747842

Reaction equation

1-naphthaleneboronic acid

4-bromoiodobenzene

sodium carbonate

→

1-(4-bromophenyl) naphthalene

Yield 81.0%

Solvents

toluene

Conditions

Workup

1. 1
   OtherAfter the reaction in the mixture
2. 2
   Filtrationfiltration
3. 3
   Dryingdried with magnesium sulfate, toluene
4. 4
   workup.DISTILLATIONwas distilled away under reduced pressure
5. 5
   Otherwas obtained with an yield of 81%

Procedure

Under an argon gas atmosphere, 200.0 g (1.163 mol) of 1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 4-bromoiodobenzene, 26.9 g (23.3 mmol) of tetrakis(triphenylphosphine) palladium(0), 3.7 L of toluene and 1.74 L of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 90 degrees C. 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 268 g of 1-(4-bromophenyl)naphthalene was obtained with an yield of 81%.

Source