Abstract: By using the economic and easily obtained industrial material 2-methoxy-5-nitroaniline as a starting material, 2-chloro-4-nitroanisole was obtained in the process of diazotization reaction and Sandmeyer reaction. Furthermore, 2-chloro-4-nitroanisole was treated with sodium hydroxide to run a nucleophilic substitution reaction, acidified by hydrochloric acid to give desired product 2-chloro-4-nitrophenol. The synthetic routine is simple and appliable. The Mulliken charges of carbons in benzene of 2-chloro-4-nitroanisole were calculated by Gaussian98 program, The results showed that the mulliken charge of the fifth carbon of benzene connected with methoxy was higher than that of other carbons, which predicts the nucleophilic substitution reaction position.