Hydrochloric Acid → HCID 57667913, compound

HRID 2191681Notes

Reaction equation

HRID 2191681 reaction equation
I[C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:18][C:19]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:20]=1[NH2:21].CN1CCOCC1.Cl>[Cu].C(OCC)(=O)C.CN(C)C=O>[F:18][C:19]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:20]=1[NH:21][C:2]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 79724-MethylmorpholineHCID 97092,4-DifluoroanilineHCID 57667966HCID 57667966, compound

Product 1

HCID 57667913HCID 57667913, compound

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To N,N-dimethylformamide 15 mL solution of 2-iodo-4-phenoxybenzoic acid 1.5 g, were added 2,4-difluoroaniline 0.67 mL, copper powder 0.084 g and N-methylmorpholine 1.2 mL, and it was stirred at 100° C. for 5 hours. After the reaction mixture was cooled to room temperature,1.0 mol/L hydrochloric acid and ethyl acetate were added to it. The organic layer was separated and collected,dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [eluent; hexane:ethyl acetate=2:1] to give 2-(2,4-difluoroanilino)-4-phenoxybenzoic acid 0.60 g of white solid.

Workup

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. customThe organic layer was separated
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-dd79eaea0c624877bd753b8b61850331
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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