Peracetic Acid → 2-(Benzenesulfonyl)-3-(trifluoromethyl)oxirane

HRID 1352353Notes

Reaction equation

HRID 1352353 reaction equation
[F:1][C:2]([F:15])([F:14])[CH:3]=[CH:4][S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=[O:7])=[O:6].C(OO)(=[O:18])C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.C(OCC)(=O)C.O1CCCC1>[C:8]1([S:5]([CH:4]2[CH:3]([C:2]([F:1])([F:14])[F:15])[O:18]2)(=[O:6])=[O:7])[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 6585Peracetic AcidHCID 11430Potassium CarbonateHCID 27779693,3,3-Trifluoro-1-(phenylsulphonyl)prop-1-ene

Product 1

HCID 211002182-(Benzenesulfonyl)-3-(trifluoromethyl)oxiraneYield 90%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 25.4 mmol 3,3,3-trifluoro-1-(phenylsulphonyl)prop-1-ene in 80 ml acetonitrile were added 30.5 mmol peracetic acid (39% solution in acetic acid) and 101 mmol potassium carbonate. The mixture was heated at 60° C. for 4 h. The reaction mixture was then diluted with ethyl acetate/tetrahydrofuran (1:1) and was washed with brine. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford the title compound as a light yellow crystalline solid (yield 90%). EI-MS (m/e): 252.0 (M+, 15%), 125.1 (PhSO+, 100%), 77.2 (Ph+, 37%).

Workup

  1. washwas washed with brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7cb81d9307074cdca9921c993309cdf6
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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