Synthesis
Part A. Synthesis of 2-bromo-4-iodoaniline
The synthesis of this compound is based on a modified method of J. Chem. Soc., Perkin Trans. 1, 1970, 2106. The specific steps are as follows:
1. 1.61 g (9.36 mmol) of o-bromoaniline was mixed with 10 mL of water and 750 mg of sodium bicarbonate solid was added.
2. Mildly heat the mixture using a hot air gun to melt the aniline.
3. 2.58 g (10.2 mmol) of powdered iodine is added in batches over several minutes. 4.
4. Stir the reaction mixture for 2 hours at room temperature. 5.
5. The resulting dark solid product is collected by filtration, washed with water and dried over air to give a slightly wetted dark solid.
6. The product was purified directly by rapid column chromatography on silica gel, eluting first with hexane and subsequently with a hexane solution containing 5% ethyl acetate to afford 2.53 g (91% yield) of the target compound 2-bromo-4-iodoaniline as a pale pink solid.
References
[1] Bulletin of the Chemical Society of Ethiopia, 2015, vol. 29, # 1, p. 157 - 162
[2] Chemical Communications, 2012, vol. 48, # 48, p. 6052 - 6054
[3] Organic and Biomolecular Chemistry, 2011, vol. 9, # 8, p. 2987 - 2991
[4] Molecules, 2005, vol. 10, # 10, p. 1307 - 1317
[5] Molecules, 2004, vol. 9, # 7, p. 617 - 621
