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 0.17 g (0.0005 mol) of tetrabutylammonium bromide are dissolved in 25 ml of methylene chloride at room temperature. 12 ml (0.02 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 4 hours during which the reaction temperature rises to 30° C. The reaction mixture is added to 50 ml of water, the phases are separated, the aqueous phase is extracted several times with methylene chloride and the combined organic phases are washed with saturated aqueous sodium chloride solution. After drying the organic phase with sodium sulfate, the volatiles are distilled off. Following distillation of the crude product in a kugelrohr (0.5 mbar, 100°-120° C. bath temperature), 1.47 g (70.5% of theory) of 2-chloro-5-trifluoroacetylpyridine are obtained.

Provenance & Evidence