Benzimidazole → Benzimidazol-1-yl-acetic acid tert-butyl ester

Participants

Reaction Steps

A solution of potassium tert-butoxide (0.6 mmol) in THF (0.6 mL) was added to a solution of 1H-benzoimidazole (71 mg, 0.6 mmol) in dioxane (15 mL) under stirring. tert-Butyl bromoacetate (97 mg, 0.5 mmol) was added to the white suspension and the mixture was stirred overnight at ambient temperature. The solvents were removed in vacuum and the product was purified on a silica gel column using a gradient of ethyl acetate in heptane) to afford benzimidazol-1-yl-acetic acid tert-butyl ester (110 mg, 95%). Mass spectrum (ESI) m/z: 233.0. 1H NMR (400 MHz, MeOD) δ ppm 1.5 (s, 9 H), 5.0 (s, 2 H), 7.3 (m, 2H), 7.4 (d, J=7.1 Hz, 1H), 7.7 (d, J=6.6 Hz, 1H), 8.1 (s, 1H).

Provenance & Evidence