4-Fluoroiodobenzene → HCID 57667991, compound

HRID 2191691Notes

Reaction equation

HRID 2191691 reaction equation
Cl.[NH2:2][C:3]1[CH:12]=[C:11]([CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].[F:27][C:28]1[CH:33]=[CH:32][C:31](I)=[CH:30][CH:29]=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[F:27][C:28]1[CH:33]=[CH:32][C:31]([NH:2][C:3]2[CH:12]=[C:11]([CH2:13][O:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:10]=[CH:9][C:4]=2[C:5]([O:7][CH3:8])=[O:6])=[CH:30][CH:29]=1

Participants

7

Reactant 3

HCID 96054-FluoroiodobenzeneHCID 10796Cesium carbonateHCID 68962145HCID 68962145, compound

Product 1

HCID 57667991HCID 57667991, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 1140TolueneSolvent

Procedure

To toluene 4.0 mL suspension of methyl 2-amino-4-(phenoxymethyl)benzoate hydrochloride 0.40 g, rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 8 mg, palladium acetate 3 mg and cesium carbonate 0.89 g was added 1-fluoro-4-iodobenzene 0.47 mL, and it was heated and refluxed under nitrogen atmosphere for 16 hours. After the reaction mixture was cooled to room temperature, insoluble matter was filtrated, 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-(phenoxymethyl)benzoate 0.22 g of pale yellow oil.

Workup

  1. temperaturewas heated
  2. temperaturerefluxed under nitrogen atmosphere for 16 hours
  3. filtrationinsoluble matter was filtrated
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-efe43bdad2e943b2b29b11cbb191db1f
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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