-Elamod is a new anti-inflammatory drug, which can be used to treat rheumatoid arthritis. Under the catalysis of potassium tert-butoxide, 4- chloro -3- nitroanisole (compound 2) reacts with phenol to produce 4- phenoxy -3- nitroanisole (compound 3). Compound 3 was reduced by nitro group to produce 4- phenoxy -3- amino anisole (compound 4). 4- phenoxy -3- methanesulfonamido anisole (compound 5) was generated from methanesulfonyl chloride in pyridine. Then aluminum trichloride and aminoacetonitrile hydrochloride are dissolved in nitrobenzene, and compound 5 is added, and saturated hydrogen chloride gas is continuously introduced for Geithmann-Koch reaction to generate α-amino -2- methoxy -4- methanesulfonamido -5- phenoxyacetophenone hydrochloride (compound 6); Compound 6 was hydrolyzed by methoxy to obtain α-formamido -2- methoxy -4- methanesulfonamido -5- phenoxyacetophenone (compound 7). Finally, compound 7 undergoes cyclization reaction with N, N- dimethylformamide dimethyl acetal to obtain the target product ilamod (compound 1). In this paper, the feed ratio and reaction time of etherification were studied. The dosage of iron powder and hydrochloric acid in reduction reaction; Effects of the dosage of methanesulfonyl chloride and pyridine on the yield of methanesulfonyl reaction products: The synthesis methods and mechanisms of Geithmann-Koch reaction, aminoacylation reaction, methoxy hydrolysis reaction and cyclization reaction were discussed. The optimum technological conditions were determined: the molar ratio of 4- chloro -3- nitroanisole/phenol/potassium tert-butoxide was 0.25/qq.wenwen/www.591lunwen.com 0.35/0.42, and the reaction temperature was 1 10℃. In the reduction reaction, every 4g of compound 3 reacts with 3g of reduced iron powder and1.2ml of 4mol L ~ (-1) hydrochloric acid at 70℃ 1h, and the yield is 82.4%. In 50mL pyridine, every 2.5g of compound 4 reacts with 1.8mL of methanesulfonyl chloride at 0℃ ~ 5℃/h, and the yield is 93.0%. The total yield of the target product (compound 1) was 37.7%.