反応 #48107

反応方程式

hydrochloric acid

triisopropyl borate

1-bromo-4-cyclopropyl-benzene

→

product

4-Cyclopropyl-phenylboronic acid

溶媒

hexane

THF

toluene

反応条件

後処理

1. 1
   workup.ADDITIONis added
2. 2
   温度The solution is warmed to −20° C.
3. 3
   温度The reaction mixture is further warmed to room temperature
4. 4
   その他the organic phase is separated
5. 5
   抽出The aqueous phase is extracted with ethyl acetate
6. 6
   乾燥the combined organic phases are dried (sodium sulphate)
7. 7
   その他The solvent is evaporated
8. 8
   洗浄the residue is washed with a mixture of ether and cyclohexane

実験手順

2.5 M nButyllithium in hexane (14.5 mL) is added dropwise to 1-bromo-4-cyclopropyl-benzene (5.92 g) in THF (14 mL) and toluene (50 mL) chilled to −70° C. The resultant solution is stirred at −70° C. for 30 min before triisopropyl borate (8.5 mL) is added. The solution is warmed to −20° C. and then treated with 4 M aqueous hydrochloric acid (15.5 mL). The reaction mixture is further warmed to room temperature and then the organic phase is separated. The aqueous phase is extracted with ethyl acetate and the combined organic phases are dried (sodium sulphate). The solvent is evaporated and the residue is washed with a mixture of ether and cyclohexane to give the product as a colorless solid.

出典