Water → 2-Chloro-4-fluoro-3-propylbenzonitrile

Temperature

100 °C

To a solution of 2-chloro-4-fluoro-3-propylbenzaldehyde (877 mg) in 1-methyl-2-pyrrolidone (15 mL) was added hydroxyammonium hydrochloride (383 mg), and the mixture was stirred at 100° C. for 1 hr. The reaction mixture was ice-cooled, thionyl chloride (1.00 mL) was added dropwise thereto, and the mixture was stirred at the same temperature for 10 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 purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=15:1→2:1) to give the title compound as a colorless oil (yield: 660 mg).

1. temperaturecooled
2. stirringthe mixture was stirred at the same temperature for 10 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 purified by silica gel column chromatography (developing solvent: hexane-ethyl acetate=15:1→2:1)

ORD record

ord-f8a6bbbf2dfb4550be7642fa51481847

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08592452B2