Uses
2''-Bromoacetanilide is used as a reagent in the preparation of furan-2-ylmethylene thiazolidinediones as novel, potent, and selective inhibitors of phosphoinositide 3-kinase γ.
Synthesis
General procedure for the synthesis of 2'-bromoacetanilide from ethanoic anhydride and o-bromoaniline: o-bromoaniline (22.0 g, 128 mmol), acetic anhydride (13.06 g, 128 mmol) and a catalytic amount of 4-dimethylaminopyridine (DMAP) were dissolved in dichloromethane (100 mL), and stirred at 0 °C. The reaction mixture was slowly warmed to room temperature and stirring was continued overnight. Upon completion of the reaction, the reaction mixture was washed with saturated aqueous sodium bicarbonate solution and subsequently concentrated. The concentrated residue was ground with a solvent mixture of hexane/dichloromethane, the solid product was collected by filtration and rinsed with hexane to give 2'-bromoacetanilide (25.4 g, 92.8% yield). The high performance liquid chromatography (HPLC) retention time (Rt) was 1.523 min.
References
[1] Journal of Medicinal Chemistry, 2003, vol. 46, # 11, p. 2187 - 2196
[2] Organic Letters, 2004, vol. 6, # 19, p. 3293 - 3296
[3] Organic Letters, 2016, vol. 18, # 22, p. 5896 - 5899
[4] Dyes and Pigments, 2018, vol. 159, p. 419 - 428
[5] Patent: US2005/192310, 2005, A1. Location in patent: Page/Page column 20
