The bromination of 4-hydroxybenzaldehyde (I) with Br2 in AcOH gives 3-bromo-4-hydroxybenzaldehyde (II), which is treated with benzoyl chloride and TEA in ethyl acetate to yield 4-(benzoyloxy)-3-bromobenzaldehyde (III). The reduction of (III) with NaBH4 in THF affords the benzyl alcohol (IV), which is treated with PBr3 in dichloromethane to provide 4-(benzoyloxy)-3-bromobenzyl bromide (V). Reaction of 4-fluorobenzonitrile (VI) with 4H-1,2,4-triazol-4-amine (VII) by means of t-BuOK in DMSO yields 4-(3H-1,2,4-triazol-4-ylamino)benzonitrile (VIII), which is condensed with compound (V) by means of NaH in DMF to give the tertiary amine (IX). Hydrolysis of the benzoate group of (IX) with KOH in methanol yields the phenol (X), which is finally treated with sulfamoyl chloride (XI) in toluene/DMA to provide the target sulfamate.

The bromination of 4-hydroxybenzaldehyde (I) with Br2 in AcOH gives 3-bromo-4-hydroxybenzaldehyde (II), which is treated with benzoyl chloride and TEA in ethyl acetate to yield 4-(benzoyloxy)-3-bromobenzaldehyde (III). The reduction of (III) with NaBH4 in THF affords the benzyl alcohol (IV), which is treated with PBr3 in dichloromethane to provide 4-(benzoyloxy)-3-bromobenzyl bromide (V). Reaction of 4-fluorobenzonitrile (VI) with 4H-1,2,4-triazol-4-amine (VII) by means of t-BuOK in DMSO yields 4-(3H-1,2,4-triazol-4-ylamino)benzonitrile (VIII), which is condensed with compound (V) by means of NaH in DMF to give the tertiary amine (IX). Hydrolysis of the benzoate group of (IX) with KOH in methanol yields the phenol (X), which is finally treated with sulfamoyl chloride (XI) in toluene/DMA to provide the target sulfamate.