Acetic Acid → 2-Bromo-3-(4-bromobutyl)thiophene

Participants

Reaction Steps

3-(4-bromobutyl)thiophene (8 g, 36.5 mmol) was dissolved in 250 ml CHCl3, and glacial acetic acid (250 ml) was added in the dark. NBS (6.5 g, 36.5 mmol) was added, and the mixture was stirred for 20 minutes at room temperature in the dark. The reaction mixture was washed with water, saturated NaHCO3, dried over magnesium sulfate and the solvent was removed under vacuum. Purification by column chromatography afforded the title compound (7.4 g, 68% yield) as a light yellow oil. 1H-NMR (ppm, CDCl3): 1.71-1.77 (2H, m), 1.85-1.89 (2H, m), 2.6 (2H, t, J=7.44 Hz), 3.43 (2H, t, J=7.32 Hz), 6.78 (1H, d, J=5.6 Hz), 7.19 (1H, d, J=5.6 Hz); 13C-NMR (ppm, CDCl3): 27.5, 29.4, 32.9, 33.9, 109.2, 125.5, 128.4, 141.8; GC-MS (m/z): 295.89.

Provenance & Evidence