Synthesis
The synthesis of 2-bromo-3-octylthiophene (10) was carried out with reference to methods reported in the literature (He M, Leslie TM, Sinicropi JA. Synthesis of Chromophores with Exceptionally High Electro-Optic Properties. 1. Thienyl- Based Bridge Chromophores. Chem Mater 2002;14:4662-8). The procedure was as follows: 3-octylthiophene (9) (5.49 g, 28 mmol) was slowly added dropwise to a solution of N,N-dimethylformamide (DMF) (30 mL) of N-bromosuccinimide (NBS) (5.76 g, 28 mmol). The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched by the addition of water (150 mL) and extracted with ethyl acetate (2 x 150 mL). The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by n-hexane column chromatography to afford the target compound 2-bromo-3-octylthiophene (10) as a colorless oil (6.95 g, 90% yield).
References
[1] Patent: WO2015/15397, 2015, A1. Location in patent: Page/Page column 51
[2] Chemistry - A European Journal, 2010, vol. 16, # 6, p. 1911 - 1928
[3] Synthetic Communications, 1999, vol. 29, # 9, p. 1607 - 1610
[4] Dyes and Pigments, 2015, vol. 121, p. 99 - 108
[5] Patent: US2010/137611, 2010, A1. Location in patent: Page/Page column 14
