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

HRID 1491966Notes

Reaction equation

HRID 1491966 reaction equation
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

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 92152Silver(II) oxideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bc80b5ab606d46ab91f0b69e0c42cbf4
Source dataset
uspto-grants-1994_12
Patent number
US05371225

Reaction notes

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