Trifluoroacetic acid → Ethyl 2-(2,2-difluoroethoxy)-4-(methylamino)-5-nitrobenzoate

Participants

Reaction Steps

A solution of 2,2-difluoroethanol (1.7 g; 20.6 mmol) in THF (50 mL) is added to a solution of ethyl 2-fluoro-4-(methylamino)-5-nitrobenzoate (5.0 g; 20.6 mmol) in DMF (100 mL). Sodium hydride (0.824 g; 60%; 20.6 mmol) is added in portions and the mixture is stirred overnight at rt. A solution of TFA (30 mL; 0.45 M aq) is added and the mixture is concentrated. The resulting precipitate is filtered off, washed with water, dried and recrystallized from EtOH/water to give the sub-title compound. Yield: 4.8 g (76%).

Provenance & Evidence