Abstract:
AIM:A new route of synthesis of benflumetol(I) by 5-step reactions was developed. METHODS: The starting material, fluorene(II), was chlorinated with chlorine to yield 2,7-dichlorofluorene(III), which underwent Friedel-Crafts acylation with chloroacetyl chloride to give 2,7-dichloro-4-chloroacetyl-fluorene(IV). IV was reduced by means of KBH4 to provide 2,7-dichlorofluorenyl-4-ethylene oxide(V) which was then condensed with dibutylamine to yield α-(dibutylaminomethyl)-2,7-dichloro-4-fluorenemethanol(VI). The final product(I) was obtained by further condensation of(VI) with
p-chlorobenzaldehyde. RESULTS: Acetylation and chloroacetylation of III, the acetyl and chloroacetyl groups entered mainly into the 4 position of fluorene nucleus by both chemical method and spectrum analysis. CONCLUSION: The reliability of this new route of synthesis was established.