反应详情

温度

80 °C

Sodium hydride (0.122 g, 5.0 mmol, 60% w/w) was washed with dry hexanes and evaporated under a stream of nitrogen. 10 mL THF was added and the mixture was cooled to 0° C. (5-Bromo-2-isopropyl-4-methoxy-phenoxy)-acetonitrile (0.577 g, 2.03 mmol) was added in portions. After 30 min ethyl formate (4.9 mL, 60.9 mmol) was added and the solution was warmed to 80° C. After 4.5 hours the mixture was cooled and 5.0 mL iodomethane was added in one portion. After 16 hours the solution was quenched with H2O, concentrated in vacuo, extracted with ethyl acetate, washed with H2O and then washed with brine. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (9:1 hexane/ethyl acetate) afforded 2-(5-bromo-2-isopropyl-4-methoxy-phenoxy)-3-methoxy-acrylonitrile (0.319 g, 48%) as a white solid.

1. customevaporated under a stream of nitrogen
2. addition10 mL THF was added
3. additionwas added in portions
4. temperatureAfter 4.5 hours the mixture was cooled
5. customAfter 16 hours the solution was quenched with H2O
6. concentrationconcentrated in vacuo
7. extractionextracted with ethyl acetate
8. washwashed with H2O
9. washwashed with brine
10. dry with materialThe combined organic layers were dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customPurification via flash chromatography (9:1 hexane/ethyl acetate)