Reacción #1747847

Ecuación de reacción

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

9-(4-bromophenyl)phenanthrene

→

4-(9-phenanthrenyl)phenylboronic acid

Rendimiento 72.4%

Disolventes

toluene

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for two hours at −60 degrees C
2. 2
   TemperaturaThe reaction solution was further cooled down to −60 degrees C
3. 3
   TemperaturaSubsequently, the reaction mixture was warmed up to room temperature
4. 4
   workup.STIRRINGstirred for 17 hours
5. 5
   TemperaturaThe reaction mixture was cooled down to 0 degree C
6. 6
   workup.STIRRINGstirred for one hour at room temperature
7. 7
   OtroAfter the reaction
8. 8
   SecadoAfter organic phase thereof was dried with magnesium sulfate
9. 9
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
10. 10
    OtroBy recrystallizing residue by toluene and hexane

Procedimiento

Under an argon gas atmosphere, a mixture of 21.3 g (63.9 mmol) of 9-(4-bromophenyl)phenanthrene and 200 mL of dehydrated THF was cooled down to −60 degrees C., and added with 49.2 mL (76.7 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 36.1 g (192 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 cooled down to 0 degree C. to be further added with solution of hydrochloric acid, and then 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 residue by toluene and hexane, 13.8 g of 4-(9-phenanthrenyl)phenylboronic acid was obtained at an yield of 72%.

Fuente