반응 #707012

반응 방정식

4-bromo-3-methylbenzonitrile

tert-butyl lithium

THF

SMe2

→

title compound

4-Hydroxy-3-methylbenzonitrile

용매

pentane

반응 조건

후처리

1. 1
   기타O2 is slowly bubbled through the reaction mixture for 30 minutes
2. 2
   온도to warm to ambient temperatures
3. 3
   workup.STIRRINGThe solution is stirred for 16 hours
4. 4
   workup.ADDITIONThe solution is then poured into 100 mL of H2O
5. 5
   workup.ADDITIONThe solution is diluted with EtOAc
6. 6
   기타The layers are separated
7. 7
   세척The organic layer is washed with saturated (NH4)2SO4 solution
8. 8
   추출The organic layer is then extracted with 10 N NaOH
9. 9
   추출The solution is then extracted with EtOAc
10. 10
    건조The combined organic layers are dried over MgSO4
11. 11
    여과filtered
12. 12
    농축concentrated

실험 절차

To a solution of 4-bromo-3-methylbenzonitrile (7.07 g, 36.1 mmol) in 225 mL of THF at -78° C. is added a 1.7 M solution of tert-butyl lithium (45.6 mL, 77.6 mmol) in pentane. After 5 minutes, CuBr.SMe2 (15.9 g, 77.6 mmol) is added. The resulting solution is stirred for 10 minutes, then O2 is slowly bubbled through the reaction mixture for 30 minutes. After this time, the solution is allowed to warm to ambient temperatures. The solution is stirred for 16 hours. The solution is then poured into 100 mL of H2O. The solution is diluted with EtOAc. The layers are separated. The organic layer is washed with saturated (NH4)2SO4 solution. The organic layer is then extracted with 10 N NaOH. The collected aqueous basic layers are acidified to pH=6 with 6N HCl. The solution is then extracted with EtOAc. The combined organic layers are dried over MgSO4, filtered and concentrated. The title compound is obtained as a solid.

출처