Hydrogen Peroxide → Trifluoromethyluracil

Participants

Reaction Conditions

Reaction Steps

1.1 g (10 mmol) of uracil was weighed and placed in a 100 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: 20 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 22.5 ml of dimethyl sulfoxide, 7.5 ml of a 2.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 2.0 ml of a 30% hydrogen peroxide aqueous solution and 3.0 ml of a 1.0 mol/l aqueous solution of iron (II) sulfate. The mixture was stirred at 40 to 50° C. for 30 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 94%) was confirmed in the same manner as in Example 1.

Provenance & Evidence