反应详情

温度

-78 °C

Under argon, 7.587 g (15.37 mmol) of 2-chloro-5-iodo-N,N-bis(4-methoxybenzyl)aniline were dissolved in 100 ml of THF and cooled to −78° C. 7.65 ml (15.27 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were then slowly added dropwise. The reaction solution was then slowly warmed to −40° C. and stirred at this temperature for 30 min. 2 g (13.97 mmol) of N-methoxy-N,1-dimethylcyclopropanecarboxamide [R. Shintani et al., Chem. Eur. J., 15 (35), 8692-8694 (2009)], dissolved in 20 ml of THF, were then slowly added dropwise to the reaction solution. The reaction mixture obtained was then slowly warmed to room temperature and stirred at this temperature overnight. 50 ml of an ice-cold saturated aqueous ammonium chloride solution were then added to the reaction mixture. After separation of the phases, the aqueous phase was extracted three more times with ethyl acetate, and the combined organic phases were dried over magnesium sulphate, filtered and evaporated to dryness. The crude product obtained was purified chromatographically on silica gel (mobile phase cyclohexane/ethyl acetate 10:1). This gave 3.977 g (63% of theory) of the title compound.

1. temperatureThe reaction solution was then slowly warmed to −40° C.
2. additionwere then slowly added dropwise to the reaction solution
3. customThe reaction mixture obtained
4. temperaturewas then slowly warmed to room temperature
5. stirringstirred at this temperature overnight
6. customAfter separation of the phases
7. extractionthe aqueous phase was extracted three more times with ethyl acetate
8. dry with materialthe combined organic phases were dried over magnesium sulphate
9. filtrationfiltered
10. customevaporated to dryness