3-Fluoro-N-methoxy-N-methylbenzamide → 3-Fluoroacetophenone

Temperature

-78 °C

A solution of 3-fluoro-N-methoxy-N-methylbenzamide (16 g, 87.4 mmol) in THF (150 mL) was cooled to −78° C. Vinylmagnesium bromide (120 mL, 120 mmol) was added slowly. The mixture was stirred at −78° C. for 10 min, at rt for 3 h, and quenched by addition of 1 N aq HCl (100 mL) at 0° C. The aqueous layer was extracted with EtOAc (100 mL). The combined organic phase was washed with brine (50 mL), dried over Na2SO4, and concentrated. The residue was purified by column chromatography to afford 1-(3-fluorophenyl)ethanone (9.7 g, yield: 75%) as a colorless oil.

1. customquenched by addition of 1 N aq HCl (100 mL) at 0° C
2. extractionThe aqueous layer was extracted with EtOAc (100 mL)
3. washThe combined organic phase was washed with brine (50 mL)
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by column chromatography

ORD record

ord-9a6a2a9eb0484c5d83ac36e7845d7145

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680093B2