2-Fluoroethanol → N-(3-chloro-4-fluorophenyl)-2-(2-fluoroethoxy)-4-methylamino-5-nitro-benzamide

Participants

Reaction Conditions

Reaction Steps

KHMDS (0.320 g, 1.60 mmol) is added to an ice-cooled mixture of N-(4-fluoro-3-chloro-phenyl)-2-fluoro-4-methylamino-5-nitro-benzoic acid amide (500 mg, 1.46 mmol), 2-fluoroethanol (0.129 ml, 2.19 mmol) and 30 ml THF. After 30 min the temperature is raised to 60° C. for 4.5 h, then it is stirred at rt overnight. Additional 2-fluoroethanol (0.129 ml, 2.19 mmol) and KHMDS (0.160 g, 0.80 mmol) are added and it is stirred for 4.5 h at 60° C. Then the mixture is diluted with satd. aq. NaHCO3-solution and the precipitate is filtered off, washed with water and dried.

Provenance & Evidence