Sodium Iodide → (R)-2-Iodo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol

Participants

Reaction Steps

A mixture of (R)-2-bromo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (880 mg, 2.2 mmol) and NaI (3.66 g, 24.4 mmol) is refluxed in acetone (35 mL) for one hour. After the mixture is filtered, the filtrate is concentrated, and the residue is separated into ethyl acetate and water. The organic phase is washed with a 25% (w/w) aqueous sodium bisulfite solution, and dried over magnesium sulfate to give the desired (R)-2-iodo-1-[4-(phenylmethoxy)-3-[(methyl-sulfonyl)amino]phenyl]ethanol (938 mg, yield: 95%).

Provenance & Evidence