Citric Acid → HCID 57668007, compound

HRID 2191679Notes

Reaction equation

HRID 2191679 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[F:19][C:20]1[CH:25]=[CH:24][C:23](I)=[CH:22][CH:21]=1.CC(C)([O-])C.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.O1CCOCC1>[F:19][C:20]1[CH:25]=[CH:24][C:23]([NH:1][C:2]2[CH:11]=[C:10]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:9]=[CH:8][C:3]=2[C:4]([O:6][CH3:7])=[O:5])=[CH:22][CH:21]=1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 96054-FluoroiodobenzeneHCID 23676156Sodium t-butoxideHCID 57667990HCID 57667990, compound

Product 1

HCID 57668007HCID 57668007, compoundYield 51.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

To dioxane 5.0 mL solution of methyl 2-amino-4-phenoxybenzoate 0.34 g were added 1-fluoro-4-iodobenzene 0.18 mL,1,1′-bis(diphenylphosphino)ferrocene 93 mg,1,1′-bis(diphenylphosphino)ferrocene palladium(II) dichloride dichloromethane complex 46 mg and sodium tert-butoxide 0.15 g at room temperature, and it was heated and refluxed under nitrogen atmosphere for 3 hours. After the reaction mixture was cooled to room temperature,10% citric acid aqueous solution and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with 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:ethyl acetate=20:1] to give methyl 2-(4-fluoroanilino)-4-phenoxybenzoate 0.036 g of colorless oil.

Workup

  1. temperatureit was heated
  2. temperaturerefluxed under nitrogen atmosphere for 3 hours
  3. customThe organic layer was separated
  4. washafter washing with saturated sodium chloride aqueous solution
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-73445d8883904479bf41745d43f7b29f
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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