Hydrochloric Acid → Ethyl benzo[b]thiophene-5-carboxylate

Participants

Reaction Conditions

Reaction Steps

A saturated solution of HCl in ethanol (15 mL) is added to benzothiophene-5-carboxylic acid (1 g, 5.44 mmol) and stirred at 80° C. overnight. The solvent is removed under reduced pressure. Diethyl ether and saturated sodium bicarbonate are added. The aqueous layer is discarded. The organic layer is washed with saturated sodium bicarbonate and water, dried (Na2SO4), filtered, and concentrated under reduced pressure to yield the title compound as a pale brown oil (1.0 g, 89%). 1H NMR (CDCl3): δ 8.54 (s, 1H), 8.01 (d, 1H, J=8.1 Hz), 7.92 (d, 1H, J=8.1 Hz), 7.51 (d, 1H, J=5.4 Hz), 7.42 (d, 1H, J=5.4 Hz), 4.42 (c, 2H, J=6.8 Hz), 1.43 (t, 3H, J=6.8 Hz).

Provenance & Evidence