6-BROMOMETHYL-2-CYANOPYRIDINE

Synthesis of 2-bromomethyl-6-cyanopyridine or compound 7Compound 4, 1 g (8.46 mmol), was dissolved in 50 mL of anhydrous carbon tetrachloride, 1.51 g (8.46 mmol) of N-bromosuccinimide and a catalytic amount of benzoyl peroxide were added, and the mixture was refluxed for 10 h under irradiation with bright light. The precipitate was filtered off, the filtrate was evaporated under reduced pressure, and the residue was subjected to column chromatography using methylene chloride–ethyl acetate (100 : 1) as eluent to isolate 6-(bromomethyl)pyridine-2-carbo-nitrile (5) and minor 6-(dibromomethyl)pyridine-2-carbonitrile. 6-(Bromomethyl)pyridine-2-carbonitrile (5). Yield 590 mg (2.99 mmol, 35percent), mp 7981°C, R f 0.45. 1 H NMR spectrum (DMSO-d 6 ), δ, ppm: 4.66 s (2H, CH 2 Br), 7.827.89 m (2H, 3-H, 5-H), 8.03 d.d (1H, 4-H, J = 7.8, 7.8 Hz). Mass spectrum: m/z 196.97 (I rel 100percent) [M + H] + . Calculated: M 196.97.

Molecular Weight:197.03
XLogP3:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:36.7
Heavy Atom Count:10
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes