반응 #48107

반응 방정식

hydrochloric acid

triisopropyl borate

1-bromo-4-cyclopropyl-benzene

→

product

4-Cyclopropyl-phenylboronic acid

용매

hexane

THF

toluene

반응 조건

후처리

1. 1
   workup.ADDITIONis added
2. 2
   온도The solution is warmed to −20° C.
3. 3
   온도The reaction mixture is further warmed to room temperature
4. 4
   기타the organic phase is separated
5. 5
   추출The aqueous phase is extracted with ethyl acetate
6. 6
   건조the combined organic phases are dried (sodium sulphate)
7. 7
   기타The solvent is evaporated
8. 8
   세척the residue is washed with a mixture of ether and cyclohexane

실험 절차

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.

출처