Citric Acid → HCID 68960562, compound

HRID 2191662Notes

Reaction equation

HRID 2191662 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.C([O-])(=O)C.[K+].[CH:28]1[CH2:32][CH2:31][CH2:30][CH:29]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OCC)(=O)C.CN(C)C=O>[CH:32]1([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][CH:29]=[CH:28]1

Participants

10

Reactant 4

HCID 311Citric AcidHCID 8882CyclopenteneHCID 517044Potassium AcetateHCID 68956988Tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate

Product 1

HCID 68960562HCID 68960562, compound

Reagents, catalysts & solvents 5

HCID 11776TriphenylphosphineCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N,N-dimethylformamide 1 mL solution of tert-butyl 4-bromo-2-(4-fluoroanilino)benzoate 0.20 g were added potassium acetate 0.16 g, tetrabutylammonium chloride 0.15 g, cyclopentene 0.24 mL, palladium acetate 3.1 mg and triphenylphosphine 3.6 mg, and it was stirred under nitrogen atmosphere at room temperature for 17 hours. Ethyl acetate and 10% citric acid aqueous solution were added to the reaction mixture. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after sequential washing with 10% citric acid 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 [eluent; hexane:toluene=5:1] to give tert-butyl 4-(2-cyclopenten-1-yl)-2-(4-fluoroanilino)benzoate 73 mg of yellow oil.

Workup

  1. customThe organic layer was separated
  2. washafter sequential washing with 10% citric acid aqueous solution and saturated sodium chloride aqueous solution
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a65e9df85e4e4c37853e8a9e39fa047c
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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