Selectfluor → (1-Bromo-3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

Participants

Reaction Steps

To a solution of (1-bromo-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (135 mg, 0.433 mmol) in acetonitrile (4 mL) was added 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (230 mg, 0.650 mmol) at 0° C. The resulting mixture was stirred at room temperature overnight, then diluted with water (10 mL), and extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine (20 mL×3), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether) to give (1-bromo-3,6-difluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (60 mg, 42%) as a yellow solid. MS cald. for C13H9BrF2O3 330, obsd. (ESI+) [(M+H)+] 331.

Provenance & Evidence