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

HRID 1586434Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:13])CSC.[O-][S:15]([C:18]([F:21])(F)[F:19])(=O)=O.F[N+]1C=CC=C[CH:24]=1.CCCCCC.C(Cl)(Cl)Cl>ClC(Cl)CCl>[CH3:24][S:15][C:18]([F:21])([F:19])[C:9]([C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])=[O:13]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 20 ml solution of 0.5 g (2.5 mmol) of 2',4'-difluoro-2-(methylthio)acetophenone [Compound (2a-1)] in 1,1,2-trichloroethane, 3.0 g (12.1 mmol) of N-fluoropyridinium triflate ("Onoda Fluorinate FP-T500", trade name; product of Chichibu Onoda Co., Ltd.) were added at an internal temperature of 80° C., followed by stirring at an internal temperature of 100° C. for one hour. After cooling, the reaction mixture was added to n-hexane. The insoluble matter 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 distilled off under reduced pressure. The residue so obtained was subjected to chromatography on a silica gel column using chloroform, whereby 0.28 g of the title Compound (2c-1) was obtained in the form of a light yellow oil (yield: 47.5%).

Workup

temperatureAfter cooling
customThe insoluble matter 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 distilled off under reduced pressure
customThe residue so obtained

Sources & evidence

ORD record: ord-7ee50cf0d8fe4cadba3e9d4c1d1dd879
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05945438

Reaction notes

Loading…