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-1982f05964284e66832aea53a8f7e9d8

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629138B2