Heat 1-bromo-4-fluoro-2-(2-iodo-benzyloxy)-benzene (50 g, 0.123 mol), sodium acetate (30.2 g, 0.369 mol), tetrabutylammonium bromide (39.6 g, 0.123 mol), and palladium acetate (1 g) in N-methylpyrrolidine (250 mL) to 60° C. Add ethyl acrylate (12.91 g, 0.129 mol) in N-methylpyrrolidine (50 mL) dropwise over 20 min. After the addition is complete, heat the reaction mixture to 145° C. for 3 h. Cool the reaction mixture to room temperature, filter through diatomaceous earth, and wash the solids with methyl t-butyl ether (2×150 mL). Dilute the filtrate with methyl t-butyl ether (0.5 L) and wash with water (0.5 L). Separate the organic layer and extract the aqueous layer with methyl t-butyl ether (2×300 mL). Wash the combined organic layers with water (2×200 mL). Dry the organic portion over magnesium sulfate, treat with charcoal, filter, wash the solids with methyl t-butyl ether (100 mL) and concentrate. Slurry the residue in isopropanol (20 mL) in a Buchi flask at 55° C. without vacuum. Add heptanes (100 mL) with stirring. Place the dark suspension in a cold room overnight. Filter the solids, rinse with cold heptane/isopropanol (9:1, 2×100 mL), then heptane (50 mL) and dry to a constant weight in a vacuum oven at 35° C. to obtain the title compound as a tan powder (22.25 g, 61%).
