Synthesis
The general procedure for the synthesis of 4-bromo-3-iodobenzotrifluoride from p-bromobenzotrifluoride was as follows: 4-bromobenzotrifluoride (35 mL, 0.25 mol) was dissolved in 100 mL of trifluoromethanesulfonic acid at room temperature. Subsequently, N-iodosuccinimide (59 g, 0.26 mol) was added in batches over a period of 5 minutes and the resulting dark-colored mixture was continued to be stirred at room temperature for 15 hours. Upon completion of the reaction, the reaction mixture was poured over 300 g of ice. After the ice was completely melted, the aqueous phase was extracted with ether (3 × 100 mL). All organic phases were combined and washed sequentially with saturated sodium carbonate solution, water and brine and then dried with anhydrous magnesium sulfate. After filtration to remove the desiccant, the solvent was evaporated and the remaining liquid was distilled under vacuum (0.25 mbar) to give 4-bromo-3-iodobenzotrifluoride (85 g, 85% yield) as a clear liquid with a boiling point in the range of 62-64 °C.
References
[1] Heterocycles, 2007, vol. 74, # C, p. 683 - 700
[2] Angewandte Chemie - International Edition, 2008, vol. 47, # 42, p. 8108 - 8111
[3] Chemistry - A European Journal, 2016, vol. 22, # 28, p. 9687 - 9692
[4] Patent: WO2006/8558, 2006, A1. Location in patent: Page/Page column 45
[5] Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480
