3'-(Trifluoromethylthio)acetophenone → HCID 59506285, compound

HRID 1098756Notes

Reaction equation

[F:1][C:2]([S:5][C:6]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)([F:4])[F:3].[OH:15]OS([O-])=O.[K+]>CO.C1COCC1.O>[F:1][C:2]([F:4])([F:3])[S:5]([C:6]1[CH:7]=[C:8]([C:12](=[O:14])[CH3:13])[CH:9]=[CH:10][CH:11]=1)=[O:15]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(3-trifluoromethylsulfanyl-phenyl)ethanone (1.4 g, 6.36 mmol) in methanol (30 ml) and THF (30 ml) a solution of oxone, monopersulfate compound (10.94 g, 17.8 mmol) in water (50 ml) was added dropwise over a period of 10 min. The reaction mixture was stirred at 60° C. for 3 days. The organic solvent was removed in vacuo and the aqueous phase was extracted with dichloromethane. Evaporation of the combined organic layers and purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (0.66 g, 44%). 1-(3-Trifluoromethanesulfonyl-phenyl)ethanone (190 mg, 12%) was obtained as a side product which was used for the synthesis of example 77.

Workup

customThe organic solvent was removed in vacuo
extractionthe aqueous phase was extracted with dichloromethane
customEvaporation of the combined organic layers and purification of the crude product by silica gel chromatography

Sources & evidence

ORD record: ord-e032b30bfad946b0b2dd8cf22f063ac6
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143242B2

Reaction notes

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