To a solution of 3-octylthiophene (65 g, 333 mmol) in DMF (200 mL) at 0C was slowly added N-bromosuccinimide (130 ) through a dropping funnel.
g, 733 mmol) in DMF (200 mL) . The mixture was stirred in the dark for 72 hours.
The reaction mixture was poured over NaOH solution (300 mL, 2.5 M) and stirred at 0C. The mixture was extracted with ether and the combined organic layers were washed with NaOH (2.5 M) and brine. .
The organic layer was dried with MgSO 4 and the solvent was evaporated to give the yellow oily product 2,5-dibromo-3-octylthiophene (86% yield, 101 g).