1,2-Ethanedithiol → 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-(1,3-dithiolan-2-yl)-1H-pyrazole-3-carbonitrile

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Reaction Steps

To the solution of 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-formyl-1H-pyrazole-3-carbonitrile (5.00 g, 13.7 mmol) in dichloromethane (100 mL) at room temperature was added N-bromosuccinimide (0.74 g, 4.1 mmol) followed by 1,2-ethanedithiol (1.98 g, 20.6 mmol). The resulting mixture was stirred at room temperature for 3.7 hr. It was then worked up by adding 2 N sodium hydroxide. The layers were separated and the organic layer was washed with brine and then dried (sodium sulfate). It was then concentrated to afford a light beige solid (7.0 g). 19F-NMR: −63.791.

Provenance & Evidence