2,6-Dibromo-4,4-bis(2-ethylhexyl)-4H-silolo[3,2-b:4,5-b']dithiophene

Synthesis

The general procedure for the synthesis of 2,6-dibromo-4,4-bis(2-ethylhexyl)-4H-silacyclopenta[3,2-B:4,5-B']dithiophene, using the compound (CAS:1089687-04-6) as a starting material, was as follows: at 10 °C, N-bromosuccinimide (NBS) (11.65 g, 65.42 mmol. 2.06 eq.) was slowly added to a solution of the compound (17.885 g, 31.76 mmol) dissolved in 350 ml of anhydrous tetrahydrofuran. The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the crude product was purified by silica gel column chromatography (eluent: n-hexane) to afford the target compound 17a (16.47 g, 90% yield) as a yellow oil.

References

[1] Journal of the American Chemical Society, 2008, vol. 130, # 48, p. 16144 - 16145
[2] Chemical Communications, 2009, # 37, p. 5570 - 5572
[3] Patent: KR2017/50088, 2017, A. Location in patent: Paragraph 0237; 0238
[4] Patent: EP2530085, 2012, A1. Location in patent: Page/Page column 11-12
[5] Organic Electronics: physics, materials, applications, 2016, vol. 39, p. 361 - 370