4-Cyclopropyl-1-fluoro-2-nitrobenzene → 5-Cyclopropyl-2-fluoroaniline

Participants

Reaction Steps

To a solution of 4-cyclopropyl-1-fluoro-2-nitrobenzene (0.700 g, 4.26 mmol) in acetic acid (6.0 mL) was added iron powder (1.0 g). The reaction mass was stirred at RT for 2 h. The reaction mass was quenched in water and basified with NaHCO3, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated to afford 0.500 g of the desired product. 1H NMR (300 MHz, DMSO d6): δ 0.50-0.52 (m, 2H), 0.83-0.85 (m, 2H), 1.71-1.74 (m, 1H), 4.97 (s, 2H), 6.21 (m, 1H), 6.44 (d, J=9.0 Hz, 1H), 6.77-6.84 (m, 1H).

Provenance & Evidence