This Article deals with the stepwise synthesis and spectroscopic characterization of some new azo benzofuran derivatives, started from the diazotization of substituted aniline coupled with 2-hydroxy benzaldehyde. On reacting of the azo of 2-hydroxy benzaldehyde with p-bromo phenacyl bromide, the benzofuran (3a-g) are obtained. The structure of the new benzofuran derivatives have been characterized by using FT-IR, 1H-NMR,13C-NMR and DEPT-135 NMR. The biological activity of some new synthesized compound was obtained by vitro anti oxidant and anti microbial activity with both Staphylococcus aureus and Escherichia coli .The results showed that the new benzofurans have mild anti oxidant activity compared to the standard ascorbic acid.