4'-Fluorobiphenyl-4-sulfonyl chloride → 4-(4-Fluorophenyl)thiophenol

HRID 1872883

反応式

HRID 1872883 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([S:20](Cl)(=O)=O)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>O1CCCC1>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([SH:20])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 27947494'-Fluorobiphenyl-4-sulfonyl chlorideHCID 21226445Aluminium lithium hydride

生成物 1

HCID 27591524-(4-Fluorophenyl)thiophenol収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Lithium aluminum hydride (0.95 grams, 25 mmole) was added in portions to a stirred solution of 4'-fluorobiphenyl-4-sulfonylchloride (2.7 grams, 10 mmole) in tetrahydrofuran (75 mL). The resulting mixture was heated at reflux for 4 hours, cooled in an ice bath and quenched by addition of 10% aqueous sulfuric acid solution (100 mL). After stirring for 30 minutes, the mixture was filtered through Celite™ and the tetrahydrofuran was removed under vacuum. The residue was diluted with water and extracted with diethyl ether. The organic layer was washed with water and brine, dried over magnesium sulfate and concentrated under vacuum to a solid. Trituration of the solid with diethyl ether, removal of insoluble material by filtration and concentrated of the filtrate provided the title compound as a yellow solid (1.4 grams, 69%).

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 4 hours
  3. temperaturecooled in an ice bath
  4. customquenched by addition of 10% aqueous sulfuric acid solution (100 mL)
  5. filtrationthe mixture was filtered through Celite™
  6. customthe tetrahydrofuran was removed under vacuum
  7. additionThe residue was diluted with water
  8. extractionextracted with diethyl ether
  9. washThe organic layer was washed with water and brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated under vacuum to a solid
  12. customTrituration of the solid with diethyl ether, removal of insoluble material
  13. filtrationby filtration
  14. concentrationconcentrated of the filtrate

出典と根拠

ORDレコード
ord-aa6ea34d921144939116c240dcbf146f
出典データセット
uspto-grants-2000_08
特許番号
US06110964

関連ノート

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