Tetrahydrofuran → 2-chloro-1-(2-ethoxyethyl)-1H-benzimidazole

Participants

Reaction Conditions

Reaction Steps

Combine 2-chloro-1H-benzimidazole (15.3 g, 100 mmol) and tetrahydrofuran (300 mL). Cool to −70° C. Add dropwise, a solution of potassium bis(trimethylsilyl)amide (200 mL, 0.5 M in toluene, 100 mmol). After 30 minutes, add 2-chloroethyl ethyl ether (22.2 g, 200 mmol) and tetrabutylammonium bromide (0.5 g). Warm to ambient temperature and heat to reflux. After 12 hours, cool to ambient temperature and add water. Separate the organic layer and extract the aqueous layer with dichloromethane. Dry the combined organic layers over Na2SO4, filter, and evaporate in vacuo to give 1-(2-ethoxyethyl)-2-chloro-1H-benzimidazole.

Provenance & Evidence