After observing these two reactions, we treated compounds 1a (scheme-1) having benzylic bromo and sulfonamide group treated under similar condition, as expected we isolated the 2a. It is understood that phthalide ring is formed, due of hydrolysis of methyl ester, the in situ generated carboxylic ion on nucleophilic attack on bromo bearing benzylic carbon, leaving the bromide ion, and followed by desulfonation to obtained 7-Amino-3H-isobenzofuran-1-one (2a). To utilize the oxidation potentials of bromine and iodine in reducing the sulfuric acid, we done a series of reaction with variation in temperature. To our surprise, when the temperature at 170 o C, we isolated the 7-Amino-4-Bromo-3H-isobenzofuran-1-one (3a). it proved 170 o C, its critical temperature where the liberated bromide ion act as reducing agent to reduce the sulfuric acid and itself oxidized to bromine/bromonium ion, which undergoes electrophilic bromination on 7-Aminophthalide (2a) to give product 3a. In this protocol, resulting in a no bromine content in the wastewater and also avoiding the sulfonated products as impurities . Encouraged by this result, we investigated these procedures with a variety of benzyl halides (table ) to explore the generality of this system (see table ). At 100 o C all substrates (1a-1j)