2-Iodophenol → 1-(3,4-Dimethoxyphenyl)-3-(2-hydroxyphenyl)propan-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(3,4-dimethoxy-phenyl)-prop-2-en-1-ol (236 mg, 1.22 mmol) in THF (2 mL) was added under a nitrogen atmosphere 2-iodophenol (267 mg, 1.22 mmol), cesium carbonate (158 mg, 0.47 mmol) and palladium(II) acetate (8 mg, 0.04 mmol). The reaction mixture was stirred for 4 h at 80° C. After cooling to ambient temperature it was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers dried over sodium sulfate. Purification by chromatography (SiO2, heptane:ethyl acetate=90:10 to 60:40) afforded the title compound (155 mg, 45%) as a colourless oil. MS m/e: 285.0 [M−H]

Provenance & Evidence