2-Chloro-4-fluoro-5-nitrobenzoic Acid → 5-Amino-2-chloro-4-fluorobenzoic acid

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Reaction Steps

A solution of 2-chloro-4-fluoro-5-nitrobenzoic acid (18.0 g, 0.0824 mol) in 75 ml of acetic acid was heated at reflux temperature. Iron powder (18.4 g, 0.328 mol) was added in several portions and the resulting suspension was cooled to room temperature and diluted with water and ethyl acetate. The mixture was filtered and the filtrate was saved. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the title compound as a tan solid. Yield: 9.00 g (58.1%); mp.: 153-155° C.; identified by NMR and mass spectral analysis.

Provenance & Evidence