Dimethylformamide → 1-(4-Fluorophenyl)pyrrole-3-carboxylic acid

Participants

Reaction Steps

N,N-Dimethylformamide (300 ml) and water (100 ml) were added to potassium permanganate (28.7 g), and 1-(4-fluorophenyl)-3-formylpyrrole (34.4 g) was added under ice cooling. Potassium permanganate (14.4 g) was further added and the mixture was warmed up to room temperature and stirred for two hours. 1N Aqueous solution of sodium hydroxide (300 ml) was added to the reaction solution and stirred at room temperature for 0.5 hour. The reaction solution was washed with ethyl acetate, neutralized by the addition of hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated, isopropylether was added to the residue and the precipitated solid was collected by filtration to give the titled compound (15.2 g).

Provenance & Evidence