Tert-Butyl nitrite → 2-Bromo-3-chloro-6-fluoropyridine

Temperature

0 °C

To a solution of 6-bromo-5-chloropyridin-2-amine (1 g, 4.82 mmol) in dichloromethane (10 mL) at 0° C. added tert-butylnitrite (1.145 mL, 9.64 mmol) followed by pyridine hydrofluoride (3 mL, 9.64 mmol) and the mixture was stirred at 0° C. for 30 minutes. The mixture was quenched with water and extracted with dichloromethane. The organic layer was washed with water and brine (25 mL each), dried over sodium sulfate, filtered, and concentrated to afford of the title compound. 1H NMR (400 MHz, CDCl3): δ 6.90-6.93 (m, 1H), 7.80-7.84 (m, 1H).

1. customThe mixture was quenched with water
2. extractionextracted with dichloromethane
3. washThe organic layer was washed with water and brine (25 mL each)
4. dry with materialdried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated

ORD record

ord-89a2ff2821fd454fa7082145654a9c3f

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09073922B2