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

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Reaction Steps

A mixture of (R)-2-bromo-1-[4-phenylmethoxy-3-[(methylsulfonyl)amino]phenyl]ethanol (12.4 g, 31 mmol) and NaI (52 g, 346 mmol) were refluxed in acetone (190 mL) for 1.75 hours. After filtration, the filtrate was concentrated to a pasty red-brown solid which was partitioned between CH2Cl2 (150 mL) and H2O (190 mL). The organic phase was washed with 150 mL ~23.5% w/w aq. sodium bisulfite and with H2O (150 mL), dried over Na2SO4 and concentrated to give the title compound (12.72 g, 91%).

Provenance & Evidence