Reaktion #1132475

Reaktionsgleichung

triisopropylborate

hexane

n-butyllithium

hydrochloric acid

2(3-bromophenyl)naphthalene

→

3-(2-naphthyl)phenylboronic acid

Ausbeute 67.9%

Lösungsmittel

toluene

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas cooled down to minus 10 degree C
2. 2
   workup.STIRRINGThen, the mixture was stirred at 0 degree C
3. 3
   workup.STIRRINGThen, the solution was stirred at room temperature for 17 hours
4. 4
   workup.STIRRINGstirred at room temperature for 1 hour
5. 5
   TrocknenAfter organic phase thereof was dried with magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled away under reduced pressure
7. 7
   SonstigeBy recrystallizing the obtained solid by toluene

Vorschrift

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 minus 10 degree C., and 600 ml (948 mmol) of hexane solution of 1.6M n-butyllithium was dropped into the mixture while the mixture was being stirred. Then, the mixture was stirred at 0 degree C. for 2 hours. The reaction solution was again cooled down to minus 78 degrees C., and 450 g (2.39 mol) of triisopropylborate was dropped into the solution. Then, the solution was stirred at room temperature for 17 hours. The reaction mixture was added with aqueous solution of hydrochloric acid and stirred at room temperature for 1 hour. The reaction mixture was added with 3 L of toluene, and 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%.

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