Ammonium fluoride → 8-(2-Fluorophenyl)-l-benzocyclooctanone

HRID 1491966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1491966
Br[CH:2]1[CH2:9][CH2:8][C:7]2[C:10](=[O:14])[CH2:11][CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4][CH2:3]1.[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[Sn](CCCC)(CCCC)CCCC.[F-].[NH4+]>CN(C)C=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Ag]=O>[F:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH:2]1[CH2:9][CH2:8][C:7]2[C:10](=[O:14])[CH2:11][CH:12]=[CH:13][C:6]=2[CH2:5][CH2:4][CH2:3]1

Komponenten

7

Edukt 3

HCID 25516Ammonium fluorideHCID 150471822-FluorophenyltributyltinHCID 190368668-Bromo-l-benzocyclooctanone

Produkt 1

HCID 676471588-(2-Fluorophenyl)-l-benzocyclooctanoneAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 92152Silver(II) oxideKatalysatorHCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

In 10 ml of dimethylformamide were dissolved 2.0 g (7.9 mmol) of 8-bromo-l-benzocyclooctanone, 0.27 g (0.23 mmol) of tetrakis(triphenylphosphine) palladium and 2.0 g (8.6 mmol) of silver oxide, 4.6 g (11.9 mmol) of o-fluorophenyltributyl tin was added thereto, and the mixture was stirred under an argon atmosphere at 120° C for 2 hours. After cooling, an aqueous solution of ammonium fluoride was added to the reaction solution, and then stirred at room temperature for 12 hours. The reaction solution was filtered through celite, washed with ethyl acetate and water, and then extracted. The organic layer was washed with saline and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then separated and purified by silica gel column chromatography [elution solvent: hexane-ethyl acetate (9:1)]to obtain 0.84 g (40%) of the desired compound.

Aufarbeitung

  1. additionwas added
  2. temperatureAfter cooling
  3. stirringstirred at room temperature for 12 hours
  4. filtrationThe reaction solution was filtered through celite
  5. washwashed with ethyl acetate and water
  6. extractionextracted
  7. washThe organic layer was washed with saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customseparated
  11. custompurified by silica gel column chromatography [
  12. washelution solvent

Quellen und Nachweise

ORD-Eintrag
ord-bc80b5ab606d46ab91f0b69e0c42cbf4
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371225

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