Hydrogen Peroxide → Trifluoromethyluracil

Participants

Reaction Steps

0.055 g (0.5 mmol) of uracil was weighed and placed in a two-neck flask and the atmosphere in the flask was replaced with trifluoromethyl iodide. The following materials were added thereinto: 2.5 ml of dibutyl sulfoxide, 0.027 ml of concentrated sulfuric acid, 0.1 ml of a 30% hydrogen peroxide aqueous solution and 0.15 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate, and the mixture was stirred for 20 minutes. During the stirring, the temperature of the reaction system rose up in the range of from 40° C. to 50° C. Thereafter, the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 0.19%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.

Provenance & Evidence