Iodine → Ethanone, 2,2-difluoro-2-iodo-1-(2-methylphenyl)-

HRID 2090687ノート

反応式

HRID 2090687 の反応式
C[Si](Cl)(C)C.Cl[C:7]([F:18])([F:17])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:9].[I:19]I.O>C(#N)C.[Zn]>[F:17][C:7]([F:18])([I:19])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:16])=[O:9]

参加物

7

反応物 4

HCID 807IodineHCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 66974611Ethanone, 2-chloro-2,2-difluoro-1-(2-methylphenyl)-

生成物 1

HCID 66974696Ethanone, 2,2-difluoro-2-iodo-1-(2-methylphenyl)-収率 63.7%

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 6342Acetonitrile溶媒

反応条件

温度
55 °C

実験手順

To a suspension of zinc (1.6 g) in acetonitrile (40 mL) were added trimethylsilyl chloride (3.1 mL) and 2-chloro-2,2-difluoro-1-(2-methylphenyl)ethanone (4.0 g), and the mixture was stirred at 55° C. for 3 hr. The reaction mixture was allowed to cool to room temperature, iodine (3.5 g) was added, and the mixture was further stirred for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with diethyl ether. The extract was washed with aqueous sodium hydrogen sulfite solution, aqueous sodium hydrogencarbonate solution and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: hexane) to give the title compound as a yellow oil (yield 2.6 g, 46%).

後処理

  1. temperatureto cool to room temperature
  2. stirringthe mixture was further stirred for 2 hr
  3. extractionthe mixture was extracted with diethyl ether
  4. washThe extract was washed with aqueous sodium hydrogen sulfite solution, aqueous sodium hydrogencarbonate solution and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (eluent: hexane)

出典と根拠

ORDレコード
ord-dbee45f8ab7240d5aaf87dd6f4986d8f
出典データセット
uspto-grants-2013_05
特許番号
US08436187B2

反応ノート

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