Hydrochloric Acid → 3-Bromo-4-chloropyridine 1-oxide

To a well stirred solution of 3-bromo-4-nitro pyridine (12.0 g, 54.794 mmol) in methanol (120 mL) was bubbled dry hydrochloride gas at about 0-5° C. for about 1-2-hours. The reaction mixture was then stirred at ambient temperature for about 6-8 hours. The solvent was evaporated under reduced pressure, the residue obtained was diluted with 20% aqueous solution of sodium hydroxide (100 mL) and extracted with dichloromethane (3×100 mL). The combined organic layer was washed with water and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give 3-bromo-4-chloro-pyridine-N-oxide as an off-white crystalline solid.