GENERAL METHODS: Lithium tert-butoxide or potassium tert-butoxide (3.0 mmol), water (2.0 mL), and acrylic acid (1.2 mmol) were sequentially added to a Schlenk reaction tube and stirred at room temperature for 10 min under nitrogen atmosphere protection. Subsequently, m-bromoanisole (1.0 mmol) and palladium(II)-imidazole complex 1 (1.0 mol%) were added. The reaction mixture was stirred at 100 °C for 12 hours. After completion of the reaction, it was cooled to room temperature and the pH was adjusted to 1 with 4 M hydrochloric acid, followed by extraction with ethyl acetate. The organic phase was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was removed by concentration under reduced pressure and the residue was purified by fast column chromatography on silica gel to afford the target product 3-methoxycinnamic acid.
[1] New Journal of Chemistry, 2015, vol. 39, # 3, p. 2052 - 2059
[2] Journal of Chemical Research, 2013, vol. 37, # 5, p. 294 - 297