Reaction #1747838

Reaction equation

2-naphthaleneboronic acid

4-bromoiodobenzene

sodium carbonate

→

2-(4-bromophenyl) naphthalene

Yield 67.0%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   OtherAfter the reaction in the mixture
2. 2
   workup.DISTILLATIONwas distilled away
3. 3
   workup.ADDITIONthe mixture was added with methanol, such that precipitated solid
4. 4
   Otherwas separated by filtration
5. 5
   OtherBy recrystallizing the obtained solid by acetic ether and methanol
6. 6
   Othersubsequently drying the solid

Procedure

Under an argon gas atmosphere, 70.0 g (407 mmol) of 2-naphthaleneboronic acid, 115.1 g (407 mmol) of 4-bromoiodobenzene, 9.40 g (8.14 mmol) of tetrakis(triphenylphosphine) palladium(0), 1.2 L of toluene and 600 mL of 2M sodium carbonate solution were mixed, and stirred for 20 hours at 90 degrees C. After the reaction in the mixture was over, toluene was distilled away therefrom, and the mixture was added with methanol, such that precipitated solid was separated by filtration. By recrystallizing the obtained solid by acetic ether and methanol and subsequently drying the solid, 77.2 g of 2-(4-bromophenyl) naphthalene was obtained with an yield of 67%.

Source