반응 #1747839

반응 방정식

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

2-(4-bromophenyl) naphthalene

→

4-(2-naphthyl)phenylboronic acid

수율 84.0%

용매

toluene

THF

반응 조건

후처리

1. 1
   workup.STIRRINGThen, the reaction mixture was stirred for one hour at −60 degrees C
2. 2
   온도Subsequently, the reaction mixture was warmed up to room temperature
3. 3
   workup.STIRRINGstirred for 18 hours
4. 4
   workup.STIRRINGto be stirred for one hour at room temperature
5. 5
   기타After the reaction
6. 6
   건조After organic phase thereof was dried with magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
8. 8
   기타By crystallizing the obtained solid by toluene

실험 절차

Under an argon gas atmosphere, a mixture of 50.0 g (177 mmol) of 2-(4-bromophenyl) naphthalene and 500 mL of dehydrated THF was cooled down to −60 degrees C., and added with 136 mL (212 mmol) of hexane solution of 1.56M n-butyllithium in drops while being stirred. Then, the reaction mixture was stirred for one hour at −60 degrees C. 99.6 g (529 mmol) of triisopropyl borate was dropped into the reaction solution at −60 degrees C. Subsequently, the reaction mixture was warmed up to room temperature, and stirred for 18 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 crystallizing the obtained solid by toluene, 33.6 g of 4-(2-naphthyl)phenylboronic acid was obtained at an yield of 84%.

출처