The general procedure for the synthesis of 3-bromothiophene from 3-bromothiophene and 1-iododecane was as follows: 2% aqueous p-toluenesulfonic acid (PTS) solution (1.5 mL) was added to a 5 mL round-bottomed flask containing zinc powder (197 mg, 3 mmol) and PdCl2(Amphos)2 (7 mg, 0.01 mmol) under argon protection. N,N,N',N'-tetramethylethylenediamine (TMEDA, 232 mg, 2 mmol), 1-iododecane (2 mmol) and 3-bromothiophene (0.5 mmol) were added sequentially at room temperature. The reaction mixture was stirred vigorously at room temperature for the indicated time. After completion of the reaction, the product was extracted with ethyl acetate (EtOAc). Silica gel (1 g) was added to the combined organic phases and the solvent was removed under vacuum. The resulting dry crude product was loaded on top of a silica gel column and the target product 3-decylthiophene was purified by column chromatography.
