Benzofuran derivatives posses a wide range of biological activities. They have been reported to have antitumour , antimicrobial activity. The 2-arylbenzo[b]furan structure is prevalent in a wide variety of biologically active natural and unnatural compounds. The present paper describes the synthesis and antibacterial activity of 7-methoxy-2- (2,4,6-trimethoxyphenyl)benzofuran-5-carbohydrazide 8 and its related intermediates from commercially available 1,3,5-trimethoxy benzene as staring material in seven steps. The title compound and its intermediates have been screened against four bacterial strains such Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus and Streptococcus pyogenes. It is observed that the title compound, benzo[b]furan carbohydrazide 8 and benzo[b]furan carboxylic acid 6 displayed excellent activities.