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

HRID 1603285

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HRID 1603285 반응식
[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]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 8058HexaneHCID 2737404N-Fluoro-4-methylpyridinium-2-sulfonateHCID 106327011-(2,4-Difluorophenyl)-2-fluoro-2-(methylsulfanyl)ethanone

생성물 1

HCID 102203472-Methylthio-2,2,2',4'-tetrafluoroacetophenone수율 47.5%

시약·촉매·용매 1

HCID 65741,1,2-Trichloroethane용매

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온도
100 °C

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-9ff763c582c047de971aa0222fe2b9e3
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05986144

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