Hydrogen Peroxide → 8-Trifluoromethylcaffeine

Participants

Reaction Conditions

Reaction Steps

0.19 g (1.0 mmol) of caffeine 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: 0.016 g (0.3 mmol) of iron powder, 2.0 ml of dimethyl sulfoxide, 2.0 ml of a 1N dimethyl sulfoxide solution of sulfuric acid, 1.0 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide 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 8-trifluoromethylcaffeine (19F-NMR yield: 37%) was confirmed by 19F-NMR with 2,2,2-trifluoroethanol as an internal standard.

Provenance & Evidence