Synthesis
General procedure for the synthesis of 2-bromo-4-methyl-5-nitroaniline using 2-bromo-4-methylaniline as starting material: first, 2-bromo-4-methylaniline (23.8 g) was completely dissolved in concentrated sulfuric acid (119 mL). Subsequently, urea nitrate (15 g) was added slowly and in small batches at a temperature maintained at 10 °C or lower. After addition, the reaction mixture was stirred continuously at 0°C for 10 minutes. Upon completion of the reaction, water (120 mL) and 5 M aqueous sodium hydroxide (205 mL) were sequentially added to the reaction solution to neutralize the reaction system. Finally, the precipitated solid product was collected by filtration to afford the target compound 2-bromo-4-methyl-5-nitroaniline (26.3 g).
References
[1] European Journal of Organic Chemistry, 2009, # 5, p. 687 - 698
[2] Journal of the American Chemical Society, 1950, vol. 72, p. 2971
[3] Kogyo Kagaku Zasshi, 1956, vol. 59, p. 1093
[4] Chem.Abstr., 1958, p. 11779
[5] Journal of the American Chemical Society, 1950, vol. 72, p. 2971
