Sulfuryl chloride → 4-Chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole

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Reaction Steps

Sulfuryl chloride (0.48 g, 3.6 mmol) was added to a solution of 3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.93 g, 3.0 mmol) in acetic acid (10 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was poured into ice water and extracted with ethyl acetate (10 ml×3). An organic layer was washed with water, dried over anhydrous magnesium sulfate and filtered to remove a desiccant, and the solvent was distilled off from the filtrate under reduced pressure. The resultant crude product was purified with a silica gel column (ethyl acetate/hexane=1/10), to give a white solid of 4-chloro-3-(2,6-dichloro-4-trifluoromethylphenyloxy)-5-methylpyrazole (0.57 g, yield: 55.0%). mp: 156-158° C.; 1H-NMR (CDCl3, TMS, ppm): δ 2.28 (s, 3H), 7.65 (s, 2H), 8.75-9.15 (br s, 1H).

Provenance & Evidence