Ethanol → Ethyl 5-bromofuran-2-carboxylate

Participants

Reaction Steps

To a stirred suspension of 8.43 g (44.14 mmol) of 5-bromo-2-furoic acid in 100 ml absolute ethanol was added 4 ml of thionyl chloride. This mixture was stirred at reflux for 3 hours and at room temperature for 18 hours. The solvent was removed in vacuo, the residual oil treated with 100 ml water and extracted with 3×75 ml ether. The combined ether extracts were washed with saturated NaHCO3 and saturated NaCl solutions and dried (MgSO4). Solvent was removed in vacuo and the residue kugelrohr distilled (60° C.; 0.4 mm) to give the captioned compound as a colorless oil. PMR (CDCl3); δ1.35 (3H, t, J~7 Hz), 4.37 (2H, q, J~7 Hz), 6.45 (1H, d, J~4 Hz), 7.1 (1H, d, J~4 Hz).

Provenance & Evidence