Cesium carbonate → HCID 68958957, compound

HRID 2191719Notes

Reaction equation

HRID 2191719 reaction equation
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.[CH:23]([CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)=[CH2:24].C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:25]1(/[CH:23]=[CH:24]/[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)[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 12757VinylcyclohexaneHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68958957HCID 68958957, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To toluene 3.0 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added vinylcyclohexane 0.15 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, 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)-2-cyclohexylvinyl)-2-(4-fluoroanilino)benzoate.

Workup

  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

Sources & evidence

ORD record
ord-e957b8011c034a3d9c0a4d91593eb7f1
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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