Synthesis
General procedure for the synthesis of 3-bromo-5-methylaniline from 3-bromo-5-nitrotoluene: 1-bromo-3-methyl-5-nitrobenzene (5 g, 23.1 mmol) was dissolved in a mixed solvent of dioxane/water (3:1, 40 mL), and zinc powder (15 g, 231 mmol) and ammonium chloride (12.3 g, 231 mmol) were added sequentially. The reaction mixture was stirred at room temperature for 4 hours. After completion of the reaction, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 3-bromo-5-methylaniline (4.0 g, 93% yield) as a brown solid. Mass spectrometry analysis showed m/z (M+H) of 186.2.
References
[1] Patent: WO2014/149164, 2014, A1. Location in patent: Paragraph 001105
[2] Chemische Berichte, 1880, vol. 13, p. 963
[3] Chemische Berichte, 1881, vol. 14, p. 417
[4] Justus Liebigs Annalen der Chemie, 1878, vol. 192, p. 203
[5] Journal of the Chemical Society, 1929, p. 1255
