Uses
2-Bromo-3',4'-dichloroacetophenone is a chemical ragent used in the synthesis of 2-aroylbenzoxazoles. As well, it is used in the synthesis of aminoarylthiazole derivatives as correctors of chloride transport defect in cystic fibrosis patients.
Synthesis
General procedure for the synthesis of alpha-bromo-3,4-dichloroacetophenone from 3,4-dichloroacetophenone: to a solution of 3,4-dichloroacetophenone (18.8 g, 0.1 mol, 1.0 eq.) in acetonitrile (100 ml) was added p-toluenesulfonic acid (25.8 g, 0.15 mol, 1.5 eq.) and N-bromosuccinimide (17.7 g, 0.1 mol. 1.0 equiv). The reaction mixture was refluxed at 80 °C for 5 hours. After completion of the reaction, the organic phase was extracted and concentrated, and purified by silica gel column chromatography to afford α-bromo-3,4-dichloroacetophenone (95% yield).
References
[1] Russian Journal of Organic Chemistry, 1994, vol. 30, # 6.1, p. 881 - 887
[2] Zhurnal Organicheskoi Khimii, 1994, vol. 30, # 6, p. 827 - 832
[3] Patent: CN107266388, 2017, A. Location in patent: Paragraph 0098; 0099; 0100
[4] ChemMedChem, 2018, vol. 13, # 11, p. 1102 - 1114
[5] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 21, p. 7146 - 7153
