Potassium Cyanide → 2-(5-Bromopyridin-3-yl)acetonitrile

Potassium cyanide (0.21 g, 3.27 mmol) was added to a solution of 3-bromo-5-chloromethyl-pyridine (0.45 g; 2.18 mmol) in DMF (10 mL). Upon completion of addition, the reaction mixture was stirred at room temperature for 16 h. After this time, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over Na2SO4, filtered and evaporated. The resulting residue was purified by silica gel column chromatography (10% ethyl acetate in hexane) to provide 2-(5-bromopyridin-3-yl)acetonitrile (200 mg, 46.5%). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.68 (d, 1H, J=2 Hz), 8.51 (d, 1H, J=2 Hz), 7.88 (t, 1H, J=2 Hz), 3.77 (s, 2H).

1. additionUpon completion of addition
2. customAfter this time, the reaction mixture was quenched with water
3. extractionextracted with ethyl acetate
4. washThe organic phase was washed with water and brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customevaporated
8. customThe resulting residue was purified by silica gel column chromatography (10% ethyl acetate in hexane)

ORD record

ord-5334431999c14bf4b61cf28f56480d07

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575184B2