Hydrogen Peroxide → 2-(Trifluoromethyl)aniline

Participants

Reaction Steps

180 μl of aniline, 5.0 ml of dimethyl sulfoxide, 4.0 ml of a 1 N dimethyl sulfoxide solution of sulfuric acid, 0.7 ml of a 3.0 mol/l dimethyl sulfoxide solution of trifluoromethyl iodide, 0.4 ml of a 30% hydrogen peroxide aqueous solution and 0.6 ml of a 1.0 mol/l aqueous solution of iron(II) sulfate were charged in a two-neck flask in which the atmosphere was replaced with argon, 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. A molecular weight and a retention time obtained by 19F-NMR and GC-MS were compared with those of a commercially available standard specimen to confirm formation of each of 2-trifluoromethylaniline (19F-NMR yield: 8.5%), 4-trifluoromethylaniline (19F-NMR yield: 7.2%) and 2,4-bis(trifluoromethyl)aniline (19F-NMR yield: 4.2%). 2-trifluoromethylaniline

Provenance & Evidence