Reaktion #325796

Reaktionsgleichung

(6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)

→

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

Ausbeute 86.0%

Lösungsmittel

water

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate (20 mL×3)
2. 2
   WaschenThe combined organic layers were washed with brine (20 mL×3)
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo
5. 5
   SonstigeThe residue was purified by flash column chromatography (30% ethyl acetate in petroleum ether)

Vorschrift

To a solution of (6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (100 mg, 0.277 mmol) in acetonitrile (3 mL) was added 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (255 mg, 0.72 mmol) at 0° C. The resulting mixture was stirred at room temperature overnight, and diluted with water, then 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 (1,6-difluoro-4-hydroxy-naphthalen-2-yl)acetic acid methyl ester (60 mg, 86%) as a yellow solid. MS cald. for C13H10F2O3 252, obsd. (ESI+) [(M+H)+] 253.

Quelle