Hydrogen Peroxide → 2-(Trifluoromethyl)aniline

HRID 1012879Notes

Reaction equation

HRID 1012879 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[F:13][C:14](I)([F:16])[F:15].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:13][C:14]([F:16])([F:15])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH2:1].[F:13][C:14]([F:16])([F:15])[C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1.[F:13][C:14]([F:16])([F:15])[C:3]1[CH:4]=[C:5]([C:14]([F:16])([F:15])[F:13])[CH:6]=[CH:7][C:2]=1[NH2:1]

Participants

9

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 6115AnilineHCID 16843Trifluoroiodomethane

Product 3

HCID 69222-(Trifluoromethyl)anilineYield 8.5%HCID 99644-(Trifluoromethyl)anilineYield 7.2%HCID 6028562,4-Bis(trifluoromethyl)anilineYield 4.2%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent3×

Procedure

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

Workup

  1. customrose up in the range of from 40° C. to 50° C
  2. customA molecular weight and a retention time obtained by 19F-NMR and GC-MS

Sources & evidence

ORD record
ord-e01fdfb736404b18a174225513c4756c
Source dataset
uspto-grants-2011_07
Patent number
US07981318B2

Reaction notes

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