Masson, EricMarzi, ElenaCottet, FabriceBobbio, CarlaSchlosser, Manfred2006-03-032006-03-032006-03-03200510.1002/ejoc.200500240https://infoscience.epfl.ch/handle/20.500.14299/227031WOS:0002327515000227345The metalation of 2,3-, 2,6-, 2,4- and 3,5-dichlorobenzotrifluorides can be readily effected with std. reagents such as lithium diisopropylamide, lithium 2,2,6,6-tetramethylpiperidide, and butyllithium at the chlorine-adjacent 4- and 3-positions and the chlorine-flanked 3- and 4-positions, resp. However, regioselectivity was secured with 2,6-dichlorobenzotrifluoride only under equilibrating conditions as the initial deprotonation occurs simultaneously at the 3- and 4-positions. 3,4-Dichlorobenzotrifluoride requires methyllithium in the presence of potassium tert-butoxide (\"LIM-KOR\" mixt.) to undergo regioselective metalation at the 2-position. All the organometallic intermediates were converted into the corresponding benzoic acids by trapping with carbon dioxide, arguably the most popular electrophile for the characterization of organometallic intermediates. [on SciFinder (R)]Carboxylic acids Role: RCT (Reactant)SPN (Synthetic preparation)PREP (Preparation)RACT (Reactant or reagent) (benzenecarboxylic; prepn. of benzoic carboxylic acids via regioselective metalations and carboxylations of dichlorobenzotrifluorides withdichlorobenzotrifluoride regioselective metalation lithiation carboxylation buttressing effect haloarenetext::journal::journal article::research article