Triethylamine → 3-Bromopyridine-2-carbonitrile

A mixture of 3-bromopyridine N-oxide (26.09 g; 150 mmol), trimethylsilyl cyanide (50 g; 504 mmol), and triethylamine (30.36 g, 300 mmol) in dry acetonitrile under nitrogen was refluxed for 20 hours. The mixture was concentrated in vacuo, the residue partitioned between methylene chloride (600 ml) 3 N sodium carbonate solution (250 ml), and the aqueous layer was extracted with 200 ml of methylene chloride. The combined organic layer was dried over sodium sulfate, concentrated in vacuo, and the residue was purified by flash chromatography (25% ethyl acetate in hexane) to afford 17.65 g (64.5%) of 3-bromo-2-cyano-pyridine as a solid, m.p. 93°-95° C.

1. temperaturewas refluxed for 20 hours
2. concentrationThe mixture was concentrated in vacuo
3. customthe residue partitioned between methylene chloride (600 ml) 3 N sodium carbonate solution (250 ml)
4. extractionthe aqueous layer was extracted with 200 ml of methylene chloride
5. dry with materialThe combined organic layer was dried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customthe residue was purified by flash chromatography (25% ethyl acetate in hexane)

ORD record

ord-5b78632147ed4d8291f03f801e77603d

Source dataset

uspto-grants-1996_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05556909