Sodium Bicarbonate → 2-Chloro-1-(5-(2,6-difluorophenyl)-4,5-dihydroisoxazol-3-yl)ethan-1-one

To a stirred solution of 3-chloro-N-hydroxy-2-oxopropanimidoyl chloride (0.89 g, 5.71 mmol) in acetonitrile (20 mL) was added 2-ethenyl-1,3-difluorobenzene (1.0 g, 7.14 mmol) and sodium bicarbonate (1.8 g, 2.14 mmol) at room temperature. The reaction mixture was stirred at room temperature for 12 h, concentrated in under reduced pressure and the resulting material was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer was separated, washed with saturated aqueous sodium chloride solution and concentrated in under reduced pressure. The resulting material was triturated with petroleum ether and filtered to provide the title product as white solid (1.1 g) melting at 82.1-83.4° C.

1. concentrationconcentrated in under reduced pressure
2. customthe resulting material was partitioned between ethyl acetate (50 mL) and water (50 mL)
3. customThe organic layer was separated
4. washwashed with saturated aqueous sodium chloride solution
5. concentrationconcentrated in under reduced pressure
6. customThe resulting material was triturated with petroleum ether
7. filtrationfiltered

ORD record

ord-58f7c26fe9144f4a865466c1ccbdc436

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08835427B2