Water → 2-Chloro-4-fluoroisophthalonitrile

Temperature

100 °C

To a solution of 2-chloro-4-fluoro-3-formylbenzonitrile (597 mg) in 1-methyl-2-pyrrolidone (10 mL) was added hydroxyammonium hydrochloride (310 mg), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was ice-cooled at 0° C., and thionyl chloride (0.735 mL) was added dropwise thereto. The mixture was stirred at the same temperature for 30 min, water was added to the mixture and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane to give the title compound as yellow crystals (yield: 503 mg).

1. temperaturecooled at 0° C.
2. stirringThe mixture was stirred at the same temperature for 30 min
3. extractionthe mixture was extracted with ethyl acetate
4. washThe extract was washed with saturated brine
5. dry with materialdried over anhydrous magnesium sulfate
6. concentrationconcentrated under reduced pressure
7. customThe residue was recrystallized from hexane

ORD record

ord-2d959a47e1454b45a70ae576f3d5d1ae

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592452B2