4 Step Synthesis of 4-Bromoacetanilide

Faculty Advisor

James Wollack



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4 Step Synthesis of 4-Bromoacetanilide

4-Bromoacetanilide was synthesized in a four step process, with benzene as the starting material. 4-Bromoacetanilide is used as a common precursor in numerous pharmaceuticals. It also has properties that, when metabolized by the body, takes the form of an analgesic. First, benzene was nitrated using nitric acid. The resulting nitrobenzene was reduced to aniline using Sn/HCl and acetylated to form acetanilide. Finally acetanilide was brominated using Br2 and acetic acid to yield 4-Bromoacetanilide. To make the reaction slightly more green, ethanol was used as a solvent instead of methanol in the recrystallization of 4-Bromoacetanilide. This is a green alternative in terms of being more cost effective, but also maintaining the same level of chemical reactivity. The synthesis of 4-Bromoacetanilide is important because, as a precursor to pharmaceuticals, it is important for chemists to find ways to perform these syntheses in a more efficient and green manner.