Hydrochloric Acid → 6-Bromo-3-chloro-2-methoxypyridine
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N([O-])=O.[Na+].[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9](N)=[CH:8][CH:7]=1.[ClH:15]>O.[Cu](Cl)Cl>[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9]([Cl:15])=[CH:8][CH:7]=1N([O-])=O.[Na+].[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9](N)=[CH:8][CH:7]=1.[ClH:15]>O.[Cu](Cl)Cl>[Br:5][C:6]1[N:11]=[C:10]([O:12][CH3:13])[C:9]([Cl:15])=[CH:8][CH:7]=1A solution of sodium nitrite (7.04 g) in water (10 mL) was added dropwise to a suspension of 6-bromo-2-methoxypyridin-3-amine (10.4 g) in concentrated hydrochloric acid (35 mL) under ice-cooling. After stirring for 10 minutes, the reaction system was added dropwise to a suspension of copper chloride (12.7 g) in concentrated hydrochloric acid (15 mL) under ice-cooling, and the mixture was stirred at 65° C. for one hour and 15 minutes. The reaction solution was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1→7:3) to give the title compound as a yellow powder (9.69 g, 85%).
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