Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 3-(4-Hydroxy-3,5-diiodo-phenyl)-acrylic acid methyl ester

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A 50 mL round bottomed flask equipped with a Teflon coated magnetic stirring bar, a reflux condenser and a rubber septum was charged with 3,5-diiodo-4-hydroxybenzaldehyde (1 g, 2.68 mmol), methyl (triphenylphosphoranylidene) acetate (1.79 g, 5.36 mmol) and benzene (30 mL). The reaction mixture was heated to a gentle reflux for 24 h. The reaction mixture was cooled to ambient temperature and concentrated to dryness. The title compound obtained was a white solid (891 mg, 78%) after the crude material was subjected to flash chromatography (SiO2, using 20% EtOAc/Hex as the eluent).

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