Description
3-Bromo-4-chloroaniline can be used as an intermediate in pharmaceutical synthesis, such as the preparation of Vismodegib, the trade name is Erivedge, the chemical name is 2-chloro-N-(4-chloro-3 -(Pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide, developed by Curis, Genentech and Evotec in cooperation, was approved by the U.S. Food and Drug Administration (FDA) on January 30, 2012 ) marketing approval as a small molecule targeted inhibitor of the Hedgehog pathway for the treatment of basal cell carcinoma.
Synthesis
Dissolve p-chloronitrobenzene in sulfuric acid aqueous solution, slowly add bromine reagent (bromine or potassium bromate), and react to obtain 3-bromo-4-chloroaniline.
References
[1] Patent: WO2005/103010, 2005, A2. Location in patent: Page/Page column 37-38
[2] Patent: WO2014/74422, 2014, A1. Location in patent: Paragraph 00183
[3] Organic Letters, 2016, vol. 18, # 11, p. 2774 - 2776
[4] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1984, vol. 38, # 10, p. 877 - 884
[5] American Chemical Journal, 1899, vol. 22, p. 247