Hydrochloric Acid → Methyl 2-(4-fluoroanilino)-4-iodobenzoate

HRID 2191633Notes

Reaction equation

HRID 2191633 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.C(O)(=O)CCCCCCCCCCCCC.N1C(C)=CC=CC=1C.[NH2:35][C:36]1[CH:45]=[C:44]([I:46])[CH:43]=[CH:42][C:37]=1[C:38]([O:40][CH3:41])=[O:39].Cl>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:35][C:36]2[CH:45]=[C:44]([I:46])[CH:43]=[CH:42][C:37]=2[C:38]([O:40][CH3:41])=[O:39])=[CH:4][CH:3]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 79372,6-LutidineHCID 11005Myristic AcidHCID 2856454-Fluorophenylboronic acid2×HCID 18929930Methyl 2-amino-4-iodobenzoate

Product 1

HCID 57667861Methyl 2-(4-fluoroanilino)-4-iodobenzoateYield 26.1%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalyst2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To toluene 20 mL suspension of 4-fluorophenylboronic acid 1.4 g, anhydrous copper(II) acetate 0.35 g and myristic acid 0.89 g was added 2,6-lutidine 0.76 mL, and it was stirred at room temperature for 5 minutes. Methyl 2-amino-4-iodobenzoate 1.8 g was added to the reaction mixture, and it was stirred at room temperature for 3 hours. 4-fluorophenylboronic acid 0.45 g and anhydrous copper(II) acetate 0.35 g were added to the reaction mixture, and it was stirred at room temperature for 8 hours. Ethyl acetate and 1.0 mol/L hydrochloric acid were added to the reaction mixture. 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=10:1] to give methyl 2-(4-fluoroanilino)-4-iodobenzoate 0.63 g of pale yellow solid.

Workup

  1. stirringwas stirred at room temperature for 3 hours
  2. stirringwas stirred at room temperature for 8 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-e4467a82ab4f4a46aba7ef9d7783959f
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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