Hydrogen Peroxide → Trifluoromethyluracil

HRID 1363433Notes

Reaction equation

HRID 1363433 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].F[B-](F)(F)F.[H+].[F:15][C:16](I)([F:18])[F:17].OO>F[B-](F)(F)F.[Fe+2].F[B-](F)(F)F.CS(C)=O>[F:15][C:16]([F:18])([F:17])[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

7

Conditions

Temperature
45 °C

Procedure

0.11 g (1.0 mmol) of uracil was 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: 0.21 ml of a 42% tetrafluoroboric acid aqueous solution, 2.0 ml of dimethyl sulfoxide, 3.0 ml of a 2.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.3 ml of a 1.0 mol/l aqueous solution of iron (II) tetrafluoroborate and 0.2 ml of a 30% hydrogen peroxide aqueous solution. The mixture was stirred at 40 to 50° C. for 20 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.

Workup

  1. customplaced in a 50 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record
ord-30bdf16ae7bc437a80c962aa88627011
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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