m-Chloroperbenzoic acid → HCID 13339624, compound

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Reaction Steps

To a solution of 11.8 g of 2-chloro-6-methoxy-4-(3,3,3-trichloro-1-methylenepropyl)pyridine containing the 2-bromo-6-methoxy-4-(3,3,3-trichloro-1-methylenepropyl)pyridine byproduct in 300 ml of chloroform was added 10.3 g of 85% m-chloro-perbenzoic acid. The solution was heated at reflux for 32 hours, cooled, and washed with 2N sodium hydroxide, water, and dried (Na2SO4). The solvent was removed in vacuo, leaving 12.5 g of crude product which was purified by high pressure liquid chromatography using 5% ethyl acetate in hexane as eluent. 5.4 g of pure product containing 16% of the bromo derivative was obtained. Analysis of the mixture was confirmed by gas-liquid chromatography, nuclear magnetic resonance spectroscopy, mass spectroscopy, and elemental analysis. Elemental analysis for the mixture:

Provenance & Evidence