Reacción #1747837

Ecuación de reacción

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

2-(3-bromophenyl) naphthalene

→

3-(2-naphthyl)phenylboronic acid

Rendimiento 67.9%

Disolventes

toluene

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for one hour at 0 degrees C
2. 2
   TemperaturaThe reaction solution was further cooled down to −78 degrees C
3. 3
   workup.STIRRINGSubsequently, the reaction mixture was stirred for 17 hours at room temperature
4. 4
   workup.STIRRINGto be stirred for one hour at room temperature
5. 5
   SecadoAfter organic phase thereof was dried with magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   OtroBy recrystallizing the obtained solid by toluene

Procedimiento

Under an argon gas atmosphere, a mixture of 212 g (748 mmol) of 2-(3-bromophenyl) naphthalene and 3 L of dehydrated THF was cooled down to −10 degrees C., and added with 600 mL (948 mmol) of hexane solution of 1.6M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at 0 degrees C. The reaction solution was further cooled down to −78 degrees C. and added with 450 g (2.39 mol) of triisopropyl borate in drops. 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. The reaction mixture was further added with 3 L of 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-(2-naphthyl)phenylboronic acid was obtained at an yield of 67%.

Fuente