Phenethyl bromide → HCID 19591605, Verbindung

HRID 849377

Reaktionsgleichung

Reaktionsgleichung von HRID 849377
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([CH2:10][C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:20](Br)[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C)C=O>[F:3][C:4]1[CH:9]=[C:8]([CH:10]([CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:11](=[O:13])[CH3:12])[CH:7]=[CH:6][C:5]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Komponenten

5

Edukt 3

HCID 7666Phenethyl bromideHCID 24758Sodium hydrideHCID 129504182-Fluoro-4-biphenylyl acetone

Produkt 1

HCID 19591605HCID 19591605, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

1.93 g of 60% oily sodium hydride was suspended in 70 ml of dimethylformamide, and a solution of 10.0 g of 2-fluoro-4-biphenylyl acetone in 30 ml of dimethylformamide, was added under cooling with ice with stirring, followed by stirring at room temperature for 50 minutes. Then, 7.20 ml of phenethyl bromide was added, followed by stirring at room temperature for 18 hours. The reaction solution was extracted by an addition of water and ethyl ether, and the organic layer was 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) to obtain 10.9 g of the above identified compound as a pale yellow oily substance.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 50 minutes
  3. stirringby stirring at room temperature for 18 hours
  4. extractionThe reaction solution was extracted by an addition of water and ethyl ether
  5. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationThe drying agent was filtered off
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1)
  10. customto obtain 10.9 g of the

Quellen und Nachweise

ORD-Eintrag
ord-ea6b6df1ac024746ab72e35576da3135
Quelldatensatz
uspto-grants-2000_01
Patentnummer
US06011174

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