2-(4-Fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile → 2-(4-Fluoro-phenyl)-1-(6-trifluoromethyl-pyridin-2-yl)-ethanone

HRID 8226

反応式

HRID 8226 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:11](=[O:22])[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]=2)C#N)=[CH:4][CH:3]=1>Br>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]=2)=[O:22])=[CH:6][CH:7]=1

参加物

3

反応物 1

HCID 219926412-(4-Fluoro-phenyl)-3-oxo-3-(6-trifluoromethyl-pyridin-2-yl)-propionitrile

生成物 1

HCID 219928752-(4-Fluoro-phenyl)-1-(6-trifluoromethyl-pyridin-2-yl)-ethanone収率 65.5%

試薬・触媒・溶媒 1

HCID 260Hydrogen Bromide溶媒

実験手順

A slurry of 2-(4-fluoro-phenyl)-3-oxo-3-(6-tri fluoromethyl-pyridin-2-yl)-propionitrile (1.4 g, 4.4 mmol) in 48% HBr is warmed to reflux for 8 h, allowed to stand at ambient temperature 16 h, then warmed at reflux for 8 h. The mixture is extracted with ether, treated with a small amount of sodium bicarbonate, extracted with ether, made basic with solid sodium hydroxide, and extracted again with ether. Ethereal extracts are combined, dried over magnesium sulfate, and concentrated in vacuo to a dark oil. The residual oil is purified on a silica gel cartridge prepared with hexane then eluted with methylene chloride to yield 816 mg (65%) of the title compound as a dark oil.

後処理

  1. temperatureto reflux for 8 h
  2. temperaturewarmed
  3. temperatureat reflux for 8 h
  4. extractionThe mixture is extracted with ether
  5. additiontreated with a small amount of sodium bicarbonate
  6. extractionextracted with ether
  7. extractionextracted again with ether
  8. dry with materialdried over magnesium sulfate
  9. concentrationconcentrated in vacuo to a dark oil
  10. customThe residual oil is purified on a silica gel cartridge
  11. customprepared with hexane
  12. washthen eluted with methylene chloride

出典と根拠

ORDレコード
ord-d6f40288404e4a31815604afe24316b9
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

読み込み中…