反应详情

4-Bromo-3-nitroanisole (10.00 g, 43.1 mmol), ethyl acrylate (5.62 mL, 51.7 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.789 g, 0.862 mmol), tri-tert-butylphosphonium tetrafluoroborate (0.500 g, 1.724 mmol), and N,N-dicyclohexylmethylamine (10.10 mL, 51.7 mmol) were mixed in 1,4-dioxane (170 mL) and placed under an argon atmosphere. The reaction mixture was stirred at room temperature for 22 hours. The reaction mixture was diluted with water and extracted twice with ethyl acetate. The combined organic layers were separated, washed with brine, dried over magnesium sulfate, and concentrated. The resulting crude product was purified via silica gel flash column chromatography eluting with 0 to 20% ethyl acetate in hexanes to yield (E)-ethyl 3-(4-methoxy-2-nitrophenyl)acrylate (5.05 g, 20 mmol, 46.5% yield) as an orange solid.

1. extractionextracted twice with ethyl acetate
2. customThe combined organic layers were separated
3. washwashed with brine
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated
6. customThe resulting crude product was purified via silica gel flash column chromatography
7. washeluting with 0 to 20% ethyl acetate in hexanes