Isobutyronitrile → 2-(6-Bromopyridin-2-yl)-2-methylpropanenitrile

Temperature

0 °C

Potassium bis(trimethylsilyl)amide (0.5 M in toluene, 200 ml, 100 mmol) was added slowly to a solution of isobutyronitrile (8.55 ml, 95.26 mmol) in toluene (200 ml) cooled down to 0° C. After complete addition, the reaction mixture was allowed to warm up to room temperature over 1 hour. The resulting mixture was added to a solution of 2,6-dibromopyridine (56.42 g, 238.15 mmol) in toluene (100 ml). The reaction mixture was stirred at room temperature for 18 hours. The crude mixture was diluted with ether, washed with a saturated aqueous solution of ammonium chloride and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as an oil (14.04 g, 65% yield).

1. additionAfter complete addition
2. temperatureto warm up to room temperature over 1 hour
3. washwashed with a saturated aqueous solution of ammonium chloride and brine
4. dry with materialThe organic phase was dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe residue was purified on silica gel by flash column chromatography

ORD record

ord-8764fadcc7904f3cbca1acbddd455613

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173635B2