Reaction #7222

Reaction equation

Ethyl-3-bromopropanoate

benzimidazole

potassium carbonate

→

ethyl-3-(benzimidazol-1-yl)propanoate

Yield 91.0%

Solvents

acetonitrile

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureto reflux for 3 days

Procedure

Ethyl-3-bromopropanoate (1.29 g, 7.1 mmol), benzimidazole (0.70 g, 5.9 mmol), and potassium carbonate (2.44 g, 17.7 mmol) were combined in anhydrous acetonitrile (60 mL) and heated to reflux for 3 days. Aqueous work-up gave ethyl-3-(benzimidazol-1-yl)propanoate (1.17 g, 91%). 1H NMR (CDCl3) δ 2.02 (s, 3H), 2.26 (m, 2H), 4.10 (t, 2H, J=6 Hz), 4.30 (t, 2H, J=6 Hz), 7.28 (br, 2H), 7.33 (br, 1H), 7.84 (br, 1H), 7.94 (br, 1H), 7.60 (br, 1H).

Source