Halogen shuffling in pyridines: Site selective electrophilic substitutions of 2-chloro-6-(trifluoromethyl)pyridine

Add time:07/11/2019    Source:sciencedirect.com

When treated with lithium diisopropylamide in tetrahydrofuran at −85 °C and subsequently with iodine, 2-chloro-6-(trifluoromethyl)pyridine is neatly converted into its 3-iodo derivative. The latter can be quantitatively isomerized to afford 2-chloro-4-iodo-6-(trifluoromethyl)pyridine. Either iodo compound can serve as the starting material for further manipulation in reaction sequences consisting of halogen/metal exchange and electrophilic trapping.

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