N-bromobutanimide → 2-Bromo-3-n-octylthiophene

Participants

Reaction Steps

3-Octylthiophene (45 g) was dissolved in DMF (327 mL). NBS (40.75 g) was dissolved in DMF (300 mL) and was subsequently added dropped to the 3-octylthiophene solution at room temperature under the darkness. The reaction mixture was subsequently stirred at room temperature overnight, slowly diluted with water (800 mL) and extracted with diethyl ether (3×300 mL). The combined organic extracts were subsequently washed with brine (2×200 mL) and water (200 mL). The organic phase was dried over anhydrous magnesium sulfate and concentrated. Vacuum distillation of the crude residue afforded the title compound as a colorless liquid (56.0 g, yield: 89%): 1H NMR (300 MHz, CDCl3, ppm) δ: 7.15-7.13(d, 1H), 6.78-6.76(d, 1H), 2.57-2.52(t, 2H), 1.59-1.54(m, 2H), 1.29-1.27(m, 10H), 0.90-0.86(t, 3H).

Provenance & Evidence