N-bromobutanimide → 2-Bromo-3-hexylthiophene

Participants

Reaction Steps

3-hexylthiophene and N-bromosuccinimide (hereinafter, referred to as ‘NBS’) in the same amount were reacted in DMF at room temperature for 15 hours to obtain 2-bromo-3-hexylthiophene (d). 12.4 g (50 mmol) of the 2-bromo-3-hexylthiophene (d) was added to a solution of 28 mL (56 mmol) of lithium diisopropylamine (hereinafter, referred to as ‘LDA’, 2.0M in THF/Hexane) in 40 mL of anhydrous THF at about −80˜−90° C. with stirring. At this temperature, the reaction was allowed to proceed for 20˜30 minutes. A solution of 10.0 g (50 mmol) of Me3SnCl in THF was added to the mixture, and was then stirred at −50° C. for 1 hour. After completion of the reaction, the reaction mixture was extracted with ether and water. The obtained organic layer was concentrated, and distilled to afford the title compound (yield: 78%) as a colorless oil. The 1H-NMR spectrum (CDCl3) of the monomer (3) is shown in FIG. 2.

Provenance & Evidence