Chlorosuccinimide → 3-(3-Chloro-4-methylphenyl)-5-(3,4,5-trichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

Participants

Reaction Steps

To a solution of 10.5 g of 3-chloro-4-methylbenzaldoxime in 50 mL of 1,2-dimethoxyethane, 9.1 g of N-chlorosuccinimide was added and the resultant mixture was stirred at 70° C. for 2 hours. Next, the reaction mixture was left to be cooled down to room temperature and to the reaction mixture, 17.0 g of 3,4,5-trichloro-1-(1-trifluoromethylethenyl)benzene, 9.3 g of potassium hydrogen carbonate and 10 mL of water were added, followed by continuing the stirring of the reaction mixture at room temperature further for 16 hours. After the completion of the reaction, the reaction mixture was diluted with 200 mL of ethyl acetate, and the diluted reaction mixture was washed with water (70 mL×1). Subsequently, the washed reaction mixture was dehydrated and dried over saturated saline and anhydrous sodium sulfate in this order and the solvent was distilled off under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with ethyl acetate-hexane (1:5) to obtain 26.2 g of the objective substance as a brown resinoid.

Provenance & Evidence