Microwave-assisted Organic Reaction Enhancement (MORE) has emerged as a new 'lead' in organic synthesis. During the studies we observed that microwave -assisted organic synthesis requires 2-4 min. of time whereas the conventional ones takes 4-6 hrs and often with poor yields. Hence, with an objective of reducing the reaction time, application of microwave technique has proved to be advantageous in case of synthesis of new benzofuran derivatives. The structures of synthesized derivatives emerged is confirmed by their IR, NMR and Mass spectra. The representative compounds synthesized with this route is further screened for anti-bacterial, analgesic, anti-inflammatory and ulcerogenic studies. In this study we have observed that the benzofuran derivatives are less ulcerogenic compared to phenyl butazone. The structural comparisons have revealed that the chloro substitution will increase the ulcerogenic toxicity.