Potassium Carbonate → HCID 58372806, compound

HRID 656774Notes

Reaction equation

HRID 656774 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=2[CH2:22][S:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:6]=1.Cl[C:31]([F:36])([F:35])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:29])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH:31]([F:36])[F:35])=[C:7]([O:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:14]=2[CH2:22][S:23][CH2:24][C:25]([F:28])([F:26])[F:27])[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 58372824HCID 58372824, compound

Product 1

HCID 58372806HCID 58372806, compound

Reagents, catalysts & solvents 1

HCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

{4-Hydroxy-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester (0.40 g, 0.92 mmol), sodium chlorodifluoroacetate (0.282 g, 1.86 mmol), and potassium carbonate (0.14 g, 1.02 mmol) were combined in DMF:H2O (8.5:1; 4.6 mL) and degassed with N2 for 15 minutes. The reaction was then stirred at 100° C. for 4 hours. After work-up with EtOAc and 1N aqueous HCl, the residue was purified by silica gel chromatography to give {4-difluoromethoxy-3-[4-nitro-2-(2,2,2-trifluoro-ethylsulfanylmethyl)-phenoxy]-phenyl}-acetic acid methyl ester.

Workup

  1. customdegassed with N2 for 15 minutes
  2. customAfter work-up with EtOAc and 1N aqueous HCl, the residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b5b5cfa5c4bc4231ae83509e16b51ade
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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