Water → 1-(6-Chloropyridin-3-yl)-2,2,2-trifluoroethanone

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Reaction Steps

2.11 g (0.01 mol) of 2-chloro-5-(2,2,2-trifluoro-1-hydroxyethyl)pyridine and 0.18 g (0.0005 mol) of tetrabutylammnonium hydrogen sulfate are dissolved in 25 ml of toluene at room temperature. 6.1 ml (0.012 mol) of an approximately 12% strength sodium hypochlorite solution are metered in within 5 minutes with vigorous stirring and the mixture is stirred for a further 2.5 hours during which the reaction temperature rises to 27° C. The reaction mixture is added to 50 ml of water, the phases are separated, the aqueous phase is extracted several times with toluene and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phases with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (0.4 mbar, 100°-115° C. bath temperature), 1.78 g (85% of theory) of 2-chloro-5-trifluoroacetylpyridine are obtained.

Provenance & Evidence