Water → 1369356-10-4

Participants

Reaction Steps

To a solution of 2-methylthiophene-3-carbaldehyde (0.204 g, 1.62 mmol, Comins, D. L.; Killpack, M. O. J. Org. Chem. 1987, 52(1), 104-109) in DMF (10 mL) was added N-bromosuccinimide (0.43 g, 2.43 mmol); the resulting mixture was stirred at rt for about 16 h and then water (75 mL) and diethyl ether (25 mL) were added. The layers were separated and the aqueous layer was extracted with diethyl ether (2×30 mL). The combined organic layers were washed with water (15 mL), dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (SiO2, diethyl ether/hexanes 1:9) to give 5-bromo-2-methylthiophene-3-carbaldehyde (0.272 g, 1.33 mmol, 82%) as a yellow oil which crystallized on standing: 1H-NMR (CDCl3, Bruker 400 MHz) δ 2.72 (3 H, s), 7.33 (1 H, s), 9.9 (1 H, s).

Provenance & Evidence