Isopropenyl acetate → 2-Fluoro-4-biphenylyl acetone

HRID 849376

反応式

HRID 849376 の反応式
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:4]([F:14])[CH:3]=1.C[O-].C([Sn+](CCCC)CCCC)CCC.C([O:33][C:34]([CH3:36])=[CH2:35])(=O)C.[F-].[K+]>C1(C)C=CC=CC=1>[F:14][C:4]1[CH:3]=[C:2]([CH2:35][C:34](=[O:33])[CH3:36])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

参加物

6

反応物 4

HCID 7916Isopropenyl acetateHCID 5210634-Bromo-2-fluoro-1,1'-biphenylHCID 522689Potassium FluorideHCID 11964040Methoxytri-n-butylstannane

生成物 1

HCID 129504182-Fluoro-4-biphenylyl acetone

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

15.0 g of 4-bromo-2-fluorobiphenyl, 25.8 ml of tributyltin methoxide, 8.96 g of isopropenyl acetate and 0.47 g of dichlorobis{tri(o-tolyl)phosphine}palladium, were dissolved in 100 ml of toluene and refluxed under heating for 2 hours. The reaction solution was left to cool to room temperature, and a saturated potassium fluoride aqueous solution was added, followed by stirring for one hour. Then the solution was subjected to celite filtration and washed with ethyl acetate. The filtrate and the washing liquid were put together. Then, the organic layer was separated and washed with a saturated sodium chloride aqueous solution and then, dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1), followed by treatment with methylene chloride-hexane, to obtain 10.6 g of the above identified compound as yellow solid.

後処理

  1. temperaturerefluxed
  2. temperatureunder heating for 2 hours
  3. waitThe reaction solution was left
  4. filtrationThen the solution was subjected to celite filtration
  5. washwashed with ethyl acetate
  6. customThen, the organic layer was separated
  7. washwashed with a saturated sodium chloride aqueous solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationThe drying agent was filtered off
  10. distillationthe solvent was distilled off under reduced pressure
  11. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1)
  12. customto obtain 10.6 g of the

出典と根拠

ORDレコード
ord-5ff20dfa283b45cd9c16cda02f7dc8d9
出典データセット
uspto-grants-2000_01
特許番号
US06011174

関連ノート

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