Synthesis
The general procedure for the synthesis of 2-bromo-3-dodecylthiophene using 3-dodecylthiophene as starting material was as follows: a solution of N-bromosuccinimide (NBS) (48 g, 0.27 mol) was prepared by dissolving it in N,N-dimethylformamide (DMF) (160 ml). This solution was added slowly dropwise to a solution of 3-dodecylthiophene (68 g, 0.27 mol) also dissolved in DMF (110 ml). The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, 750 ml of water was added to the mixture to quench the reaction. Subsequently, multiple extractions with ether (3 x 300 ml) were performed to separate the organic phase. The combined organic phases were washed sequentially with saturated saline and deionized water, and then dried by adding anhydrous magnesium sulfate to remove residual water. After drying, the solvent was removed by rotary evaporation, and the crude product obtained was subjected to reduced pressure distillation at 125 °C/5 mmHg to finally obtain 2-bromo-3-dodecylthiophene (84.85 g, 94% yield).
References
[1] Journal of Polymer Science, Part A: Polymer Chemistry, 2011, vol. 49, # 9, p. 1933 - 1941
[2] Patent: US2010/236631, 2010, A1. Location in patent: Page/Page column 9-10
[3] Journal of the American Chemical Society, 2008, vol. 130, # 27, p. 8580 - 8581
[4] Journal of the American Chemical Society,
[5] Journal of the American Chemical Society, 2009, vol. 131, p. 5586 - 5608
