Treatment of 4-hydroxy-3-methoxybenzoic acid (I) with thionyl chloride and then with diisopropyl amine provided amide (II). Alkylation of (II) with 1,4-dibromobutane and potassium carbonate in acetonitrile, followed by treatment with sodium iodide afforded iodobutylether (III). Then, alkylation of 2-fluoro-4-hydroxybenzonitrile (IV) with iodide (III) in the presence of sodium hydride in DMF gave (V), which was condensed with acetone oxime (VI) and potassium tert-butoxide to provide (VII). Finally, cyclization of (VII) in a refluxing hydroalcoholic solution of HCl generated the target benzisoxazole.