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ChemicalBook CAS DataBase List 2,5-Dibromo-3-hexylthiophene
116971-11-0

2,5-Dibromo-3-hexylthiophene synthesis

6synthesis methods
3-Hexylthiophene

1693-86-3

2,5-Dibromo-3-hexylthiophene

116971-11-0

The general procedure for the synthesis of 2,5-dibromo-3-hexylthiophene from 3-hexylthiophene is as follows: first, 1070 g of a 48% solution of hydrobromic acid was added to 338 g of 3-hexylthiophene. The reaction mixture was cooled to -5 °C and 400 g of a 34% hydrogen peroxide solution was added slowly and dropwise over a period of 7 hours. After the dropwise addition was completed, the reaction mixture was gradually warmed to 20°C over 16 hours. After completion of the reaction, phase separation was carried out. The resulting crude product 2,5-dibromo-3-hexylthiophene had a purity of 96.9% and a yield of 97%.

-

Yield:-

Steps:

Multi-step reaction with 2 steps
1.1: magnesium / diethyl ether / 2 h / 20 °C / Inert atmosphere
1.2: 20 °C / Inert atmosphere; Cooling with acetone-dry ice
2.1: N-Bromosuccinimide / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

References:

Lee, Eunji;Hammer, Brenton;Kim, Jung-Keun;Page, Zachariah;Emrick, Todd;Hayward, Ryan C. [Journal of the American Chemical Society,2011,vol. 133,# 27,p. 10390 - 10393]

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