aniline - Electrophilic Aromatic Substitution- Bromination...

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Electrophilic Aromatic Substitution- Bromination of Aniline Name : Jordan Gales Teaching Assistant: Mathieu Chellat Lab: T/R 11:30 a.m. – 410 CE Submitted: March 4, 2010 Purpose: To synthesize 2, 4, 6-tribromoaniline via an electrophilic aromatic substitution reaction between aniline, potassium bromate, hydrobromic acid and acetic acid. Reaction Scheme : Procedure : 1 A solution of aniline ( 0.093 g, 1.00 mmol, 0.09 mL), potassium bromate (0.167 g, 1.00 mmol,) glacial acetic acid ( 3.15 g, 52.41 mmol, 3.0 mL), and Hydrobromic acid ( 0.89 g, 11.05 mmol, 0.60 mL) were reacted at room temperature (23°C) for 30 min. The reaction mixture was then quenched with cold water (10 mL). The reaction mixture was then allowed to stir for 5 min and sodium bisulfate was then added to the reaction mixture (2.5 mL). The solid product was then isolated via vacuum filtration. The crude product was then recrystallized in hot methanol using semi-micro scale technique to obtain 2,4,6 tribromoaniline ( 0.12 g, 0.37 mmol, 37%) as a white
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aniline - Electrophilic Aromatic Substitution- Bromination...

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