Chemical Properties
Beige to brown needles and crystalline powder
Uses
4-Bromo-3-fluoroaniline is a intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4
,4"-alkoxyalkylterphenyls.
Uses
4-Bromo-3-fluoroaniline is an intermediate used for the synthetic preparation of Tradizolid and various pharmaceuticals such as the synthesis of several lateral difluoro-substituted 4,4"-dialkyl- and 4,4"-alkoxyalkylterphenyls.
Synthesis
General procedure for the synthesis of 4-bromo-3-fluoroaniline from 3-fluoro-4-bromoacetanilide: N-(4-bromo-3-fluorophenyl)acetamide (12.9 g, 12.9 mmol) was dissolved in ethanol (30 mL), and stirred until completely dissolved. Subsequently, concentrated hydrochloric acid (15 mL) was added to the solution and the reaction was refluxed at 80 °C for 4 hours. Upon completion of the reaction, the reaction mixture was diluted with ice water and extracted with ethyl acetate. The organic layers were combined and washed sequentially with water and brine solution. Finally, the solvent was removed by vacuum distillation to afford 4-bromo-3-fluoroaniline (2.45 g, 100.0% yield) as an off-white solid.
References
[1] Patent: WO2014/202580, 2014, A1. Location in patent: Page/Page column 97; 98
[2] Molecular Crystals and Liquid Crystals (1969-1991), 1991, vol. 204, p. 43 - 64
[3] Journal of the Chemical Society, 1958, p. 2815,2818
