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

HRID 1603285

反応式

HRID 1603285 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 102203472-Methylthio-2,2,2',4'-tetrafluoroacetophenone収率 47.5%

試薬・触媒・溶媒 1

HCID 65741,1,2-Trichloroethane溶媒

反応条件

温度
100 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-9ff763c582c047de971aa0222fe2b9e3
出典データセット
uspto-grants-1999_11
特許番号
US05986144

関連ノート

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