反応 #155677

反応方程式

triisopropyl borate

2-iodophenanthrene

n-butyllithium

hydrochloric acid

→

phenanthrene-2-boronic acid

収率 58.7%

溶媒

ether

hexane

ether

反応条件

後処理

1. 1
   温度was increased to 0° C
2. 2
   温度The reaction solution was cooled to −60° C. again
3. 3
   workup.STIRRINGThe reaction solution was continuously stirred for 5 hours while its temperature
4. 4
   温度was increased to room temperature
5. 5
   workup.STIRRINGthe mixture was stirred for 1 hour
6. 6
   その他The water layer was removed
7. 7
   洗浄the organic layer was washed with water
8. 8
   乾燥a saturated salt solution, and was then dried with magnesium sulfate
9. 9
   その他After magnesium sulfate had been separated by filtration
10. 10
    濃縮the organic layer was concentrated
11. 11
    洗浄The resultant solid was washed with hexane and toluene

実験手順

Under an argon atmosphere, 98 g of 2-iodophenanthrene and 3 L of dehydrated ether were loaded, and then the reaction solution was cooled to −60° C. After that, 210 mL of a 1.6-M solution of n-butyllithium in hexane were added to the reaction solution. The reaction solution was stirred for 1 hour while its temperature was increased to 0° C. The reaction solution was cooled to −60° C. again, and then a solution of 151 g of triisopropyl borate in 100 mL of dehydrated ether was dropped to the reaction solution. The reaction solution was continuously stirred for 5 hours while its temperature was increased to room temperature. Subsequently, 1 L of a 10% aqueous solution of hydrochloric acid was added to the reaction solution, and then the mixture was stirred for 1 hour. The water layer was removed, and the organic layer was washed with water and a saturated salt solution, and was then dried with magnesium sulfate. After magnesium sulfate had been separated by filtration, the organic layer was concentrated. The resultant solid was washed with hexane and toluene. Thus, 42 g of phenanthrene-2-boronic acid as a target were obtained (in 58% yield).

出典