Water → HCID 59438446, compound

HRID 2177512Notes

Reaction equation

HRID 2177512 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[OH:14].C(=O)([O-])[O-].[K+].[K+].Cl[C:23]([F:29])([F:28])C(OC)=O.O>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:5]=1[O:14][CH:23]([F:29])[F:28]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 73935Methyl chlorodifluoroacetateHCID 349235methyl 2-hydroxy-4-(trifluoromethyl)benzoate

Product 1

HCID 59438446HCID 59438446, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 500 mg (2.271 mmol) 2-hydroxy-4-trifluoromethyl-benzoic acid methyl ester (CAS: 345-28-8) in 5 ml N,N-dimethylformamide at room temperature, was added 470.8 mg (3.407 mmol) potassium carbonate, followed by dropwise addition of 293.4 ul (2.725 mmol) methyl chlorodifluoroacetate. The reaction mixture was heated at 65° C. oil bath for 22 hours. Water and ethyl acetate were added. The organic phase was washed 3 times with water. The organic phase was dried over sodium sulfate, filtered and concentrated in vacuo to provide 449 mg of the title compound as a pink oil which was used in the next step without any further purification.

Workup

  1. washThe organic phase was washed 3 times with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6893d70e224b4b10816092f4014a7afe
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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