4-Bromo-2-fluoro-N-methoxy-N-methylbenzamide → 1-(4-Bromo-2-fluorophenyl)propan-1-one

Into a 1000-mL 4-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-bromo-2-fluoro-N-methoxy-N-methylbenzamide (60 g, 229.01 mmol, 1.00 equiv) in tetrahydrofuran (200 mL). To the resulting mixture was then added ethylmagnesium bromide (2M) (185 mL, 1.60 equiv) dropwise with stirring at −20° C. The resulting solution was stirred for 2 h at room temperature, then cooled to 0° C. with a water/ice bath. The reaction was then quenched by the addition of NH4Cl/H2O (500 mL). The resulting solution was extracted with ethyl acetate (3×300 mL) and the organic layers combined. The resulting mixture was washed with water (1×300 mL) and brine (1×300 mL), then dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:20) to yield 1-(4-bromo-2-fluorophenyl)propan-1-one as a white solid.

1. customInto a 1000-mL 4-necked round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. temperaturecooled to 0° C. with a water/ice bath
4. customThe reaction was then quenched by the addition of NH4Cl/H2O (500 mL)
5. extractionThe resulting solution was extracted with ethyl acetate (3×300 mL)
6. washThe resulting mixture was washed with water (1×300 mL) and brine (1×300 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. concentrationconcentrated under vacuum

ORDレコード

ord-db2804452e47483aacc0c6e15ec425be

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08822447B2