Sodium Iodide → 4-(2-Iodoethyl)-2-methoxyphenyl acetate

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A 6:4 mixture of 2-methoxy-4-(2-{[(4-methylphenyl)sulfonyl]oxy}ethyl)phenyl acetate and 4-(2-hydroxyethyl)-2-methoxyphenyl acetate (1.57 g, 4.31 mmol) and sodium iodide (0.706 mL, 17.2 mmol) in dry acetone (28 mL) was stirred at room temperature overnight with protection from light. The acetone was removed in vacuo and the residue was triturated with toluene and filtered through a plug of Celite to remove insoluble inorganic material. The filtrate was concentrated in vacuo to afford the crude product. This was purified by flash chromatography (Biotage Horizon, 40M, Si, ˜30 mL/min, 100% hexanes for 360 mL, gradient to 50% EtOAc in hexanes over 4536 mL) to give 4-(2-iodoethyl)-2-methoxyphenyl acetate. Rf=0.58 (20% EtOAc/hexanes). LCMS calc.=321.0; found=320.7 (M+H)+.

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