Potassium Hydroxide → 5-Bromo-2-methoxypyridine
Reaktionsgleichung
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[Br:11]Br.C([O-])(O)=O.[Na+]>O.[K+].[Br-]>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[N:6][CH:7]=1Komponenten
7
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][N:6]=1.[Br:11]Br.C([O-])(O)=O.[Na+]>O.[K+].[Br-]>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([O:4][CH3:3])=[N:6][CH:7]=1
To a solution of KOH (4.2 g, 0.075 mol) in water (750 mL) was added 2-methoxypyridine 16-1 (16.4 g, 0.15 mol) followed by a dropwise addition of bromine (24 g, 0.15 mol) in 1N aqueous KBr (750 mL) and the resulting solution was stirred at room temperature for 5 hr. Solid NaHCO3 was added until basic and the solution was extracted with CHCl3 (3×500 mL). The organic layer was washed with 10% NaHSO3, then brine, dried over Na2SO4, filtered, and the solvent removed in vacuo. The resulting dark brown oil was predominantly the desired compound 16-2 and was used as such in the next step.
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