反应 #48107

反应方程式

hydrochloric acid

triisopropyl borate

1-bromo-4-cyclopropyl-benzene

→

product

4-Cyclopropyl-phenylboronic acid

溶剂

hexane

THF

toluene

反应条件

后处理

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
   其他the organic phase is separated
5. 5
   萃取The aqueous phase is extracted with ethyl acetate
6. 6
   干燥the combined organic phases are dried (sodium sulphate)
7. 7
   其他The solvent is evaporated
8. 8
   洗涤the residue is washed with a mixture of ether and cyclohexane

实验过程

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.

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