Hydrogen Peroxide → 2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide

HRID 62625Notes

Reaction equation

[C:1]1([S:7][CH:8]=[C:9]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[C:10]([F:13])([F:12])[F:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:22]O.C1(C)C=CC=CC=1.O>C(O)(=O)C>[C:1]1([S:7]([CH:8]=[C:9]([C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[C:16]([Cl:21])[CH:15]=2)[C:10]([F:13])([F:11])[F:12])=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-(3,5-Dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfide (1.00 g, 94% purity, 2.69 mmol) was dissolved in glacial acetic acid (5 mL) and hydrogen peroxide (0.54 mL, 35% in water, 6:19 mml) was added in one portion. The reaction mixture was heated to 50° C. and stirred for three hours at that temperature. After cooling, toluene and water were added and the phases were separated. The aqueous phase was extracted with toluene and the combined organic phases were washed two times with saturated sodium bicarbonate solution and once with sodium metabisulfite solution (30% w/w solution in water). Drying over sodium sulfate, filtration and evaporation yielded 2-(3,5-dichlorophenyl)-3,3,3-trifluoroprop-1-en-1-yl phenyl sulfoxide (950 mg, 94% purity, 91% yield, E/Z=93/7).

Workup

temperatureAfter cooling
customthe phases were separated
extractionThe aqueous phase was extracted with toluene
washthe combined organic phases were washed two times with saturated sodium bicarbonate solution
dry with materialDrying over sodium sulfate, filtration and evaporation

Sources & evidence

ORD record: ord-636fa11e54fc4c18875dd412a4bd8cee
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447036B2

Reaction notes

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