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

✍ Scribed by Antonella Bochicchio; Lucia Chiummiento; Maria Funicello; Maria Teresa Lopardo; Paolo Lupattelli

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 986 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.03.072

✦ Synopsis

Acetylation/Sonogashira cross-coupling reaction/cyclization has been carried out in one-pot using a Na 2 PdCl 4 /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-bromophenols obtaining 2,5-disubstituted-benzo[b]furans in good yields.