Furan nitra with nitric acid in acetic anhydride, however, due to its poor aromaticity, is attacked by nucleophiles in the medium at its 5-position and requires a final stage of basic treatment or heating to restore aromaticity.

Stage 1. Generation of the electrophyte

nitration-furan-01

Stage 2. Nucleophilic attack of furan on nitronium acetate

nitration-furan-02

Step 3. Nucleophilic addition of acetate

nitration-furan-03

Stage 4. Recovery of aromaticity

nitration-furan-04