Cesium carbonate → tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate

HRID 2191721Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2191721
Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)[CH:3]=1.[CH2:23]([CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1)[CH:24]=[CH2:25].C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:26]1([CH2:23]/[CH:24]=[CH:25]/[C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:3]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Komponenten

6

Edukt 3

HCID 10796Cesium carbonateHCID 75027AllylcyclohexaneHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Produkt 1

HCID 68964903tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added allylcyclohexane 0.17 mL, cesium carbonate 0.36 g, tetrabutylammonium bromide 53 mg and polymer-carried bis(acetato)triphenylphosphine palladium(II) 86 mg at room temperature, and it was stirred at 110° C. for 22 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, and ethyl acetate and 10% citric acid aqueous solution were added to it. The organic layer was separated and collected, dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 4-((E)-3-cyclohexyl-1-propenyl)-2-(4-fluoroanilino)benzoate.

Aufarbeitung

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationinsoluble matter was filtrated
  3. additionethyl acetate and 10% citric acid aqueous solution were added to it
  4. customThe organic layer was separated
  5. customcollected
  6. dry with materialdried over anhydrous magnesium sulfate
  7. washafter sequential washing with 10% citric acid aqueous solution, saturated sodium thiosulfate aqueous solution and saturated sodium chloride aqueous solution
  8. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-d95569c415a94a17a8ae2274a8e6729f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08327467B2

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