2-Fluoro-5-nitro-3-picoline

Synthesis

22280-56-4

2751-90-8

19346-46-4

2-Chloro-3-methyl-5-nitropyridine (15 g, 86.9 mmol, purchased from Maybridge Chemical Co.), potassium fluoride (12 g, 258 mmol), and tetraphenylphosphonium bromide (20 g, 47.7 mmol, purchased from Aldrich) were mixed in 200 mL of acetonitrile and the reaction was heated to reflux for 4 days. After completion of the reaction, the reaction mixture was diluted with ether (500 mL) and filtered, and the filtrate was concentrated to obtain the crude product. The crude product was ground with hot hexane (4 x 200 mL), the hexane solutions were combined and concentrated to afford the target compound 2-fluoro-3-methyl-5-nitropyridine as a solid (8.4 g, 60% yield). The product was identified by 1H NMR (DMSO-d6, 300 MHz): δ 2.42 (s, 3H), 8.43 (m, 1H), 8.95 (dd, J = 1.6 Hz, 1H); mass spectrum (CI/NH3) m/z: 157 (M + H)+.

References