Isobutyronitrile → HCID 67451277, compound

To a 0° C. solution of 2,6-difluoropyridine (69.6 g, 605 mmol, 1.0 equiv) and isobutyronitrile (41.7 g, 610 mmol, 1.0 equiv) in toluene (500 mL) was added sodium hexamethyldisilazide (2.0 M in THF, 302 mL, 605 mmol, 1.0 equiv) in a dropwise manner. The resulting mixture was allowed to slowly warm to room temperature and stirred overnight. The reaction was then quenched with water (500 mL), and the organic layer was separated from the aqueous layer. The aqueous layer was extracted with EtOAc (2×300 mL), and the combined organic phases were washed with saturated brine solution (2×400 mL), dried over Na2SO4, concentrated to give a crude yellow oil, and chromatographed with silica gel (2-10% EtOAc/hex) to give 2-(6-fluoropyridin-2-yl)-2-methylpropanenitrile (55.7 g, 56%) as a clear oil.

1. customThe reaction was then quenched with water (500 mL)
2. customthe organic layer was separated from the aqueous layer
3. extractionThe aqueous layer was extracted with EtOAc (2×300 mL)
4. washthe combined organic phases were washed with saturated brine solution (2×400 mL)
5. dry with materialdried over Na2SO4
6. concentrationconcentrated
7. customto give a crude yellow oil
8. customchromatographed with silica gel (2-10% EtOAc/hex)

ORD record

ord-f69bc28c834b4cc88b97e34731b87eac

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09018223B2