Chloroacetyl chloride → 2-Chloro-N-[2-(chloromethyl)-6-(trifluoromethyl)phenyl]acetamide

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Reaction Steps

A slurry of 19.85 g (0.0947 mol) of 2-(chloromethyl)-6-(trifluoromethyl) anilinium chloride (prepared as in Example 1 from 20.0 g of sulfoxide) was refluxed in ethylene dichloride with 11.2 g (0.0991 mol) of chloroacetyl chloride for 30 minutes followed by addition of 1.0 g (0.0089 mol) of additional CAC and further reflux for 30 minutes. The virtually clear solution was then cooled to room temperature, washed with 10% aqueous sodium carbonate (80 ml) and dried using sodium sulfate. Evaporation and drying gave 22.14 g of white 2'-(chloromethyl)-6'-(trifluoromethyl)-2-chloroacetanilide assaying 93.5% for an overall yield from sulfoxide of 85.7%.

Provenance & Evidence