Water → HCID 118113314, compound

HRID 1485075Notes

Reaction equation

HRID 1485075 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:15])([F:14])[F:13])[C:5]([O:7][CH3:8])=[O:6].Cl[C:17]([F:22])([F:21])C([O-])=O.[Na+].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(OCC)(=O)C>[F:21][CH:17]([F:22])[O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[C:12]([F:13])([F:14])[F:15])[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734985Sodium chlorodifluoroacetateHCID 15109490Benzoic acid, 3-hydroxy-4-(trifluoromethyl)-, methyl ester

Product 1

HCID 118113314HCID 118113314, compoundYield 79.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of methyl 3-hydroxy-4-(trifluoromethyl)benzoate (see WO 2007/129745) (2.00 g), sodium chlorodifluoroacetate (2.08 g) and potassium carbonate (2.51 g) in N,N-dimethylformamide (30.0 mL) was stirred at 100° C. for 6 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with water three times and thereafter dried over anhydrous magnesium sulfate. After removing the desiccant by filtration, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-85:15) to give methyl 3-(difluoromethoxy)-4-(trifluoromethyl)benzoate as a colorless oil (1.96 g).

Workup

  1. temperatureAfter cooling the reaction mixture to room temperature
  2. washThe combined organic layers were washed with water three times
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the
  5. filtrationdesiccant by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=98:2-85:15)

Sources & evidence

ORD record
ord-5d32ae3dddce4178b3a5171b361e1349
Source dataset
uspto-grants-2016_08
Patent number
US09422240B2

Reaction notes

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