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

HRID 1586434

반응식

HRID 1586434 반응식
[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]

참가 물질

6

반응물 4

HCID 6212ChloroformHCID 8058HexaneHCID 2724576Pyridinium, 1-fluoro-, 1,1,1-trifluoromethanesulfonate (1:1)HCID 106557171-(2,4-Difluorophenyl)-2-(methylsulfanyl)ethan-1-one

생성물 1

HCID 102203472-Methylthio-2,2,2',4'-tetrafluoroacetophenone수율 47%

시약·촉매·용매 1

HCID 65741,1,2-Trichloroethane용매

반응 조건

온도
100 °C

실험 절차

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%).

후처리

  1. temperatureAfter cooling
  2. customThe insoluble matter 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 distilled off under reduced pressure
  8. customThe residue so obtained

출처 및 근거

ORD 기록
ord-7ee50cf0d8fe4cadba3e9d4c1d1dd879
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05945438

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