Efficient synthesis of 5-nitro-benzo[b]furans via 2-bromo-4-nitro-phenyl acetates

Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na2PdCl4/2-(di-tert-butylphosphino)-N-phenylindole/CuI system in TMEDA to give 5-nitro-2-substituted benzo[b]furans in excellent yields. We also describe the extension of this method to 4-EWG-2-bromo-phenols obtaining 2,5-disubstituted-benzo[b]furans in good yields.

Graphical abstractHigh efficiency was achieved by one-pot acetylation/Sonogashira cross-coupling/cyclization reactions of 4-NO2-2-bromo-phenols and terminal acetylenes in the preparation of 5-nitro-2-substituted-benzo[b]furans.Download full-size image