Réaction #1747843

Équation de réaction

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

1-(4-bromophenyl) naphthalene

→

4-(1-naphthyl)phenylboronic acid

Rendement 68.9%

Solvants

toluene

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for two hours at −60 degree C
2. 2
   workup.STIRRINGSubsequently, the reaction mixture was stirred for 17 hours at room temperature
3. 3
   workup.STIRRINGto be stirred for one hour at room temperature
4. 4
   AutreAfter the reaction
5. 5
   SéchageAfter organic phase thereof was dried with magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   AutreBy recrystallizing the obtained solid by toluene

Mode opératoire

Under an argon gas atmosphere, a mixture of 208.8 g (737.4 mmol) of 1-(4-bromophenyl) naphthalene and 2.1 L of dehydrated THF was cooled down to −60 degrees C., and added with 567 mL (884.9 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for two hours at −60 degree C. 416 g (2.21 mol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was stirred for 17 hours at room temperature. The reaction mixture was further added with solution of hydrochloric acid to be stirred for one hour at room temperature. After the reaction, the reaction mixture was further added with toluene, so that aqueous phase thereof was eliminated. After organic phase thereof was dried with magnesium sulfate, the solvent was distilled away under reduced pressure. By recrystallizing the obtained solid by toluene, 126 g of 4-(1-naphthyl)phenylboronic acid was obtained at an yield of 67%.

Source