Hydrochloric Acid → 2-(Chloromethyl)-6-(trifluoromethyl) anilinium chloride

Participants

Reaction Conditions

Reaction Steps

Chlorine (76.0 grams, 1.07 mol) was bubbled into a mechanically stirred solution of 221.0 grams (1.00 mol) of 2-(methylthiomethyl)-6-(trifluoromethyl) aniline in 2 liters of ethylene dichloride over 60 minutes while maintaining the reaction temperature below 20° C. The mixture was then heated to 60° C. while maintaining a steady stream of HCl bubbling through. Water (25 ml, 1.4 mol) was added and the HCl treatment was maintained at 60° C. for 15 minutes at which point a clear solution was obtained. Excess water was removed by azeotropic distillation (780 ml of solvent were removed) and the resulting solution was cooled to 0° C. with a steady stream of HCl bubbling through to precipitate the anilinium chloride salt. Filtration, washing of the solids with 150 ml. of cold ethylene dichloride and air-drying gave 228.0 grams (92.7%) of off-white 2-(chloromethyl)-6-(trifluoromethyl) anilinium chloride.

Provenance & Evidence