反应 #1747847

反应方程式

triisopropyl borate

hexane

n-butyllithium

hydrochloric acid

9-(4-bromophenyl)phenanthrene

→

4-(9-phenanthrenyl)phenylboronic acid

收率 72.4%

溶剂

toluene

THF

反应条件

后处理

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

实验过程

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%.

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