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

When treated with lithium diisopropylamide in THF at -85 Deg and subsequently with iodine, 2-chloro-6-(trifluoromethyl)pyridine is neatly converted into its 3-iodo deriv. The latter can be quant. isomerized to afford 2-chloro-4-iodo-6-(trifluoromethyl)pyridine. Either iodo compd. can serve as the starting material for further manipulation in reaction sequences consisting of halogen/metal exchange and electrophilic trapping. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 39, 13, 1749-1752
Year:
1998
Keywords:
Note:
CAN 128:257314
27-16
Heterocyclic Compounds (One Hetero Atom)
Section de Chimie,Universite,Lausanne,Switz.
Journal
0040-4039
written in English.
100-52-7 (Benzaldehyde); 39890-95-4 (2-Chloro-6-(trifluoromethyl)pyridine) Role: RCT (Reactant), RACT (Reactant or reagent) (regioselective electrophilic substitution of chloro(trifluoromethyl)pyridine); 205444-23-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (regioselective electrophilic substitution of chloro(trifluoromethyl)pyridine); 205240-59-1P; 205444-18-4P; 205444-19-5P; 205444-20-8P; 205444-21-9P; 205444-22-0P; 205444-24-2P Role: SPN (Synthetic preparation), PREP (Preparation) (regioselective electrophilic substitution of chloro(trifluoromethyl)pyridine)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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