Hydrogen Peroxide → 5,6-Bis(trifluoromethyl)uracil

Participants

Reaction Conditions

Reaction Steps

0.18 g (1.0 mmol) of 6-trifluoromethyluracil and 0.058 g (0.3 mmol) of ferrocene were weighed and placed in a 50 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 1.8 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 2.1 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 60 to 70° C. for 20 minutes and then the resulting solution was cooled to room temperature. Formation of 5,6-bis(trifluoromethyl)uracil (19F-NMR yield: 63%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard. 5,6-Bis(trifluoromethyl)uracil was obtained as a white solid (0.12 g, yield: 48%) by preparative thin-layer chromatography.

Provenance & Evidence