4-Bromo-3-fluoro-N-methoxy-N-methylbenzamide → 1-(4-Bromo-3-fluorophenyl)ethan-1-one

Temperature

0 °C

To a solution of 4-bromo-3-fluoro-N-methoxy-N-methylbenzamide (58.5 g, 0.223 mol) in tetrahydrofuran (500 mL) was added 3.00 M of methylmagnesium chloride in tetrahydrofuran (125 mL, 0.38 mol) at 0° C. The mixture was stirred for 1 h at 0° C., and was quenched with cold saturated NH4Cl solution (150 mL). The organic layer was separated and concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL). The aqueous layer was diluted with water (100 mL) and was extract with ethyl acetate (3×50 mL). The organic solution and extracts were combined, washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure to give product (48.4 g, 99%) which was directly used in next step without further purification.

1. customwas quenched with cold saturated NH4Cl solution (150 mL)
2. customThe organic layer was separated
3. concentrationconcentrated under reduced pressure
4. additionThe residue was diluted with ethyl acetate (100 mL)
5. additionThe aqueous layer was diluted with water (100 mL)
6. extractionwas extract with ethyl acetate (3×50 mL)
7. washwashed with brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-931a8bd0a86c4244b100da6ca08b56e9

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07683060B2