Hydrogen Peroxide → 2-Chloro-3-fluoropyridine 1-oxide
反応式
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N:3]=1.OO.S(=O)(O)[O-:12].[Na+]>C(O)(=O)C>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-:12]参加物
5
反応条件
- 温度
- 75 °C
実験手順
A mixture of 2-chloro-3-fluoropyridine (11.8 g, 0.10 mol) and 11.4 ml of 30% hydrogen peroxide in acetic acid, 70 ml, is stirred at 75° C. for 4 hours. Additional 30% hydrogen peroxide, three 5 ml portions, is added over 24 hours followed by 3 ml of a saturated sodium bisulfite solution. The reaction mixture is concentrated to approximately 25 ml under reduced pressure at 55°-60° C., diluted with water, 30 ml, and made basic with potassium carbonate. The crude N-oxide is extracted into ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. Chromatography over silica gel and elution with 2% MeOH- 98% CHCl3 (v/v) mixture gives 2-chloro-3-fluoropyridine N-oxide as a liquid.