Sodium Carbonate → (E)-ethyl-3-(4'-chloro-biphenyl-4-yl)-but-2-enoate

Participants

Reaction Steps

Tetrakis(triphenylphoshine)palladium(0) (0.26 g, 0.22 mmol, 4 mol %) was added, under nitrogen, to a stirred solution of (E)-ethyl 3-(4-bromophenyl)-but-2-enoate (1.5 g, 5.57 mmol) {prepared as detailed in example 50 a} in DME (70 ml), and the resulting orange coloured solution stirred at room temperature for 10 min. Aqueous 2M sodium carbonate (16.7 ml, 33.4 mmol) was then added, the mixture stirred for 10 min, then 4-chlorophenyl boronic acid (1.3 g, 8.36 mmol) was added, and the reaction mixture heated to 80° C. for 18 h, under reflux. The reaction mixture was diluted with 1N HCl (100 ml) and the products extracted into ethyl acetate (2×100 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product, which was purified by column chromatography on silica gel (20% ethyl acetate in n-heptane eluent) to give the product, (E)-ethyl-3-(4′-chloro-biphenyl-4-yl)-but-2-enoate as a colourless solid; 1.17 g (70%).

Provenance & Evidence