Nitrogen → 2-(3-Ethoxy-buta-1,3-dienyl)-5-hydroxy-benzonitrile

Participants

Reaction Steps

To a stirred solution of 2-bromo-5-hydroxy-benzonitrile (1.4 g, 7.1 mmol), ethyl acrylate (2.12 g, 21.2 mmol), palladium(II) acetate (0.159 g, 7.0 mmol), diisopropylethylamine (0.82 g, 14.1 mmol), and tri-ortho-tolylphosphine (0.430 g, 14.1 mmol) was added propionitrile (50 mL). The reaction was stirred overnight at 80° C. under a stream of N2. The mixture was cooled, filtered, and concentrated. The crude material (3.0 g) was purified by radial chromatography (10-70% EtOAc/hexanes) to give the title compound as a white solid (1.1 g). MS [EI] m/z 216 (M+H)+.

Provenance & Evidence