Aromatic Nucleophilic Substitution: The Reaction of Sodium 2,2,2-Trifluoroethoxide with Chlorobenzonitriles in HMPA

Abstract

The preparation¹ of fluorinated compounds continues to be of significant interest to organic chemists due to their diverse and important application as polymers, blood substitutes, pharmaceuticals and pesticides. Considerable attention has been directed to the formation of fluoroalkoxy benzenes with the majority of the synthetic routes involving the reaction of an electrophilic haloalkyl fluoride with a nucleophilic phenol derivative^1,2. In a somewhat related procedure, Mendel³ has prepared ortho-2,2,2-trifluoroethoxy methyl benzoate by reacting ortho-hydroxy methyl benzoate with 2,2,2-trifluoroethyl trifluoromethylsulfonate in a potassium carbonate/acetone mixture.