Synthesis
General procedure for the synthesis of 5-fluoro-2,4-dinitroaniline from 1,5-difluoro-2,4-dinitrobenzene: 2.0 equivalents (1.02 mL) of ammonia were slowly added dropwise to a solution of 1.0 equivalents (4.0 mmol) of 1,5-difluoro-2,4-dinitrobenzene (DFDNB, 1) dissolved in 40 mL of THF under magnetic stirring. The reaction mixture was continued to be stirred at room temperature for 30 min. After removing the solvent by evaporation under reduced pressure, water was added to precipitate the product. The crude product 5-fluoro-2,4-dinitroaniline (2) was collected by filtration and washed well with water. The target product 5-fluoro-2,4-dinitroaniline was finally obtained in 99% yield and >99% purity by HPLC.
References
[1] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 14, p. 4189 - 4192
[2] Recueil des Travaux Chimiques des Pays-Bas, 1916, vol. 35, p. 142
[3] Chem. Zentralbl., 1913, vol. 84, # II, p. 760
