1,8 - naphthalimide compound fluorescent material is important. In this paper, 4,5 - two pairs of methyl acetylene to replace benzene -1,8 - naphthalimide synthesis were studied. Acenaphthene as raw materials in order to tar by bromination, oxidation, condensation, and other steps of the synthesis of 4,5 - dibromo-replace -1,8 - naphthalimide. Using Sonogashira reaction to Pd (PPh3) 2Cl2 as a catalyst, CuI as catalyst, 4,5 - dibromo -1,8 - naphthalimide as raw materials in ethanol solvent in the synthesis of 4,5 - 2 pairs of methyl replace acetylene benzene -1,8 - naphthalimide, using nuclear magnetic resonance method of structural characterization of compounds. Study of different solvents, temperature, reaction time, oxidant amount on the effects of oxidation. Discussion of the catalyst, cocatalyst, solvent, and various substituted aryl halogen compounds on the impact of Sonogashira coupling reaction.