2-fluoro-N-methoxy-N-methylbenzamide → 1-(2-Fluorophenyl)prop-2-en-1-one

Temperature

-78 °C

A solution of 2-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 slowly added, and the mixture stirred at −78° C. for 10 min, slowly warmed to rt, and stirred for another 3 h. The reaction mixture was quenched with 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-(2-fluorophenyl)-prop-2-en-1-one (7.6 g, yield: 58.4%) as a colorless oil.

1. temperatureslowly warmed to rt
2. stirringstirred for another 3 h
3. customThe reaction mixture was quenched with 1 N aq HCl (100 mL) at 0° C
4. extractionThe aqueous layer was extracted with EtOAc (100 mL)
5. washThe combined organic phase was washed with brine (50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. customThe residue was purified by column chromatography

ORD record

ord-a004043b1205498793e83b26da1a5c18

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08629138B2