Chloroform → 2-Methylthio-2,2,2',4'-tetrafluoroacetophenone

HRID 1603285

Reaction equation

[CH3:1][S:2][CH:3]([F:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=[O:5].[F:15][N+]1C=CC(C)=CC=1S([O-])(=O)=O.CCCCCC.C(Cl)(Cl)Cl>ClC(Cl)CCl>[CH3:1][S:2][C:3]([F:15])([F:14])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][C:7]=1[F:13])=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

In a 20 ml solution of 0.5 g (2.3 mmol) of 2-methylthio-2,2',4'-trifluoroacetophenone [Compound (2b-1)] in 1,1,2-trichloroethane, 0.7 g (3.7 mmol) of N-fluoro-4-methylpyridinium-2-sulfonate ("MEC-02", trade name; Daikin Industries, Ltd.) was added at an internal temperature of 80° C., followed by stirring at an internal temperature of 100° C. for 20 minutes. After cooling, the reaction mixture was added to n-hexane. The insoluble matter so precipitated was filtered off. The insoluble matter was then washed with ethyl ether, followed by combination with the hexane layer. The layers so combined were washed successively with water and saturated saline, followed by drying over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column using chloroform, whereby 0.26 g of the title Compound (2c-1) was obtained in the form of a light yellow oil (yield: 48.1%).

Workup

temperatureAfter cooling
customThe insoluble matter so precipitated
filtrationwas filtered off
washThe insoluble matter was then washed with ethyl ether
washThe layers so combined were washed successively with water and saturated saline
dry with materialby drying over anhydrous magnesium sulfate
distillationThe solvent was then distilled off under reduced pressure
customThe residue so obtained

Sources & evidence

ORD record: ord-9ff763c582c047de971aa0222fe2b9e3
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05986144

Linked notes

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