Réaction #1747841

Équation de réaction

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

1-(3-bromophenyl) naphthalene

→

3-(1-naphthyl)phenylboronic acid

Rendement 71.9%

Solvants

toluene

THF

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for two hours at −60 degrees C
2. 2
   TempératureThe reaction solution was further cooled down to −60 degrees C
3. 3
   TempératureSubsequently, the reaction mixture was warmed up to room temperature
4. 4
   workup.STIRRINGstirred for 17 hours
5. 5
   workup.STIRRINGto be stirred for one hour at room temperature
6. 6
   AutreAfter the reaction
7. 7
   SéchageAfter organic phase thereof was dried with magnesium sulfate
8. 8
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
9. 9
   AutreBy recrystallizing the obtained solid by toluene

Mode opératoire

Under an argon gas atmosphere, a mixture of 200.0 g (706.3 mmol) of 1-(3-bromophenyl) naphthalene and 2.1 L of dehydrated THF was cooled down to −60 degrees C., and added with 543 mL (847 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 degrees C. The reaction solution was further cooled down to −60 degrees C. and added with 398.5 g (2.119 mol) of triisopropyl borate in drops. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 17 hours. 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 3-(1-naphthyl)phenylboronic acid was obtained at an yield of 67%.

Source