A solid-phase approach to fluorobenzimidazoles 6a and fluoro-2-hydroxyquinoxalines 6b has been achieved by a new strategy of 'one-bead-two-compound'. The precursor, 6-nitro-2,3,4,5- tetrafluorobenzoic acid, was tagged to Rink amide MBHA resin via an α-amino acid linker. The first nucleophilic substitution generated two regioisomers in which the second active fluorine atom underwent a subsequent nucleophilic substitution with a primary amine. The reduction of the aryl nitro groups with SnCl2·2H2O/NMM and the formation of a five-membered ring with aldehydes afforded 4b and 5a. Fluorobenzimidazoles 6a were directly furnished by cleavage using TFA, therewith the stable six-membered ring 6b was produced by concomitant intramolecular cyclization and thermal dehydrogenation. In addition to introduction of fluorine into the heterocycles, two scaffolds could be simultaneously synthesized with this method.