[Synthesis]
The general procedure for the synthesis of 2-(3-methoxyphenyl)furan from 2-furanylboronic acid and m-bromoanisole is as follows: referring to the method of Oxford et al, [3] furan-2-boronic acid (168 mg, 1.5 mmol, 1.5 equiv), m-bromoanisole (1.0 mmol, 1.0 equiv), tetrakis(triphenylphosphine)palladium (116 mg, 0.1 mmol. 10 mol%) and cesium carbonate (350 mg, 1.1 mmol, 1.1 eq.) were suspended in a toluene/methanol solvent mixture (4:1, 10 mL, v/v). The reaction mixture was stirred at 100 °C for 16 hours. After completion of the reaction, the reaction mixture was diluted with ethyl acetate (8 mL), the organic layer was separated, washed with saturated saline (20 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography. |