Journal
JOURNAL OF FLUORINE CHEMISTRY
Volume 131, Issue 11, Pages 1241-1246Publisher
ELSEVIER SCIENCE SA
DOI: 10.1016/j.jfluchem.2010.06.013
Keywords
Fluorination; Lewis acid; Antimony pentachloride; alpha alpha alpha Trichlorotoluene; Chloro trichlorotoluene; HF base
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The selective fluorination by successive Cl/F exchanges of alpha alpha alpha-trichlorotoluene substituted or not by a chlorine atom was studied in the presence of HF as the fluorin long agent The influence of the presence of a catalyst or a basic solvent (such as dioxane pyridine tributylphosphate) in order to control the fluorination was also investigated In mild conditions (50 C and after 1 h of reaction) HF in excess was required in order to obtained the trifluoromethylation by Cl/F exchanges The presence of SbCl5 in small amount activated the Cl/F exchanges and only a stoichiometric amount of HF was required whatever the chlorinated molecules Selective mono and difluorination could be obtained by using basic solvents (C) 2010 Elsevier B V All rights reserved
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