Li Zi-ying
2008
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Journal
Chemical Reagents
Abstract
2-Bromo-4-nitrophenol was synthesized by using 2-methoxy-5-nitroaniline as the starting material via diazotization reaction and the Sandmeyer reaction to yield 2-bromo-4-nitroanisole,which was further treated with sodium hydroxide to realize a nucleophilic substitution reaction,with the product acidified by hydrochloric acid to obtain the desired product 2-bromo-4-nitrophenol.The target product yield was 55.8%.An optimized process was obtained by investigating the influence of the ratio of solvents and reactants on nucleophilic substitution reaction.The synthetic pathway was simple,efficient and suitable for commercial production.The net electric charges of carbons in benzene ring of 2-bromo-4-nitroanisole were calculated by the Gaussian 03 program.The results showed that the net electric charge of carbon in benzene ring connected with methoxy group was the highest than any other,which predicted the nucleophilic substitution reaction position.