A synthesis of useful intermediate, 2-(azidomethyl)-5-bromobenzofuran starting from 5-bromobenzofuran-2-carboxylic acid is described. The reaction of 5-bromo-2-(iodomethyl)benzofuran with sodium azide affords 2-(azidomethyl)-5-bromobenzofuran. 5-Bromo-2-(iodomethyl)benzofuran was obtained from a combination of consecutive 5-bromobenzofuran-2-carboxylic acid reactions involving NaBH4 reduction followed by the iodination of the resulting alcohol. The utility of 2-(azidomethyl)-5-bromobenzofuran has been demonstrated for the preparation of a novel series of 1-((5-bromobenzofuran-2-yl-)methyl)-4-substituted phenyl-1H-1,2,3-triazoles in excellent yields. The newly synthesized compounds have been characterized and evaluated for antimicrobial activities against Gram-negative and Gram-positive bacterial strains.