N-Iodosuccinimide → (6-Fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester

Participants

Reaction Steps

To a solution of (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (600 mg, 2.56 mmol, the product of 8th step for example 1-1) in chloroform (260 mL) was added N-iodosuccinimide (577 mg, 2.56 mmol) at 0° C. The mixture was allowed to warm to room temperature and stirred at room temperature for 2 hours. The resulting mixture was diluted with 10% aqueous solution of sodium bisulfate (100 mL). The organic layer was separated, washed with brine (100 mL), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column (elution with 15% ethyl acetate in petroleum ether) to afford (6-fluoro-4-hydroxy-3-iodo-naphthalen-2-yl)-acetic acid methyl ester (500 mg, 54%) as a white solid.

Provenance & Evidence