Ethyl Acrylate → HCID 86694134, compound

Participants

Reaction Steps

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.

Provenance & Evidence