반응 #168217

반응 방정식

3-chloro-5-(4-phenoxyphenyl)isonicotinonitrile

3-chloroperbenzoic acid

→

3-chloro-4-cyano-5-(4-phenoxyphenyl)pyridine 1-oxide

수율 63.1%

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   세척washed with 1 M sodium sulfite (25 mL), 1 N NaOH (2×25 mL)
2. 2
   건조dried (MgSO4)
3. 3
   농축concentrated
4. 4
   세척eluting with 20-50% ethyl acetate in hexanes

실험 절차

A solution of 3-chloro-5-(4-phenoxyphenyl)isonicotinonitrile (0.495 g, 1.614 mmol) and 77% 3-chloroperbenzoic acid (1.808 g, 8.07 mmol) in dichloromethane (20 mL) was stirred at room temperature. After 22 h at room temperature, the mixture was diluted with dichloromethane (100 mL), washed with 1 M sodium sulfite (25 mL), 1 N NaOH (2×25 mL), brined (25 mL), dried (MgSO4) and concentrated. Silica gel chromatography, loading with dichloromethane and eluting with 20-50% ethyl acetate in hexanes, gave 3-chloro-4-cyano-5-(4-phenoxyphenyl)pyridine 1-oxide as white solid (328.8 mg, 63% yield). 1H NMR (400 MHz, CDCl3) δ ppm 8.25 (1H, δ, J=1.51 Hz), 8.16 (1H, δ, J=1.51 Hz), 7.46-7.58 (2H, m), 7.36-7.45 (2H, m), 7.21 (1H, t, J=7.40 Hz), 7.03-7.16 (4H, m); MS (ES+) m/z: 323 (M+H); LC retention time: 3.863 min (analytical HPLC Method A).

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