Methyl Acrylate → HCID 58288194, compound

Participants

Reaction Conditions

Reaction Steps

Under argon, 119.5 g (1.39 mol) of methyl acrylate were added dropwise to a mixture of 100 g (0.463 mol) of 2-bromo-6-nitrotoluene, 323 ml (2.31 mol) of triethylamine, 28.2 g (92.6 mmol) of tri-2-tolylphosphine and 10.4 g (46.3 mmol) of palladium(II) acetate in 2.0 liters of DMF, and the mixture was then stirred at 125° C. for 36 h. After cooling to room temperature, the reaction mixture was stirred with 4 liters of saturated aqueous ammonium chloride solution and extracted three times with a total of 5 liters of diethyl ether. The combined organic phases were washed with water and saturated sodium chloride solution and dried over sodium sulphate. After filtration, the solvent was removed to dryness under reduced pressure. The residue obtained was purified by flash chromatography on silica gel (mobile phase petroleum ether/ethyl acetate 6:1). The product was triturated with heptane, and the solid obtained was filtered off with suction and dried under high vacuum. This gave 48.7 g of the title compound (46.6% of theory).

Provenance & Evidence