Réaction #1747838

Équation de réaction

2-naphthaleneboronic acid

4-bromoiodobenzene

sodium carbonate

→

2-(4-bromophenyl) naphthalene

Rendement 67.0%

Solvants

toluene

toluene

Conditions de réaction

Traitement

1. 1
   AutreAfter 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
   Autrewas separated by filtration
5. 5
   AutreBy recrystallizing the obtained solid by acetic ether and methanol
6. 6
   Autresubsequently drying the solid

Mode opératoire

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