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New 2-(α-fluorobenzyl)benzimidazole derivatives have been prepared. Fluorination was carried out from benzylic alcohols using 2-chloro-1,1,2-trifluorotriethylamine reagent. The scope and the rates of formation of the resulting products are dependent on the nature of the substituents. Physical data, 1 H and 19 F NMR chemical shifts of the hydroxy and fluorine compounds are given.