Methanol → 3-Isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]aniline

HRID 604814Notes

Reaction equation

HRID 604814 reaction equation
[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[C:12](F)([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[NH2:8])[CH:2]([CH3:4])[CH3:3].[CH3:22][OH:23]>C[O-].[Na+]>[CH2:1]([C:5]1[CH:6]=[C:7]([CH:9]=[CH:10][C:11]=1[C:12]([O:23][CH3:22])([C:17]([F:20])([F:19])[F:18])[C:13]([F:16])([F:15])[F:14])[NH2:8])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 866190023-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline

Product 1

HCID 866190033-Isobutyl-4-[1-methoxy-2,2,2-trifluoro-1-(trifluoromethyl)ethyl]anilineYield 79.6%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

3-Isobutyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]aniline (1.6 g, 5 mmol) was dissolved in a 28% by weight methanol solution (9.6 g) of sodium methoxide and stirred under heating for 3 hours. After cooling, the reaction solution was poured into ice water, followed by extracting with ethyl acetate and washing with water. The solution was dried over magnesium sulfate and concentrated under reduced pressure, and then the residue was purified by using silica gel chromatography (hexane:ethyl acetate=5:1) to obtain 1.31 g of the desired compound.

Workup

  1. temperatureunder heating for 3 hours
  2. temperatureAfter cooling
  3. extractionby extracting with ethyl acetate
  4. washwashing with water
  5. dry with materialThe solution was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customthe residue was purified

Sources & evidence

ORD record
ord-234ae70c77394c1eaa6259bddb267e2d
Source dataset
uspto-grants-2011_03
Patent number
US07910735B2

Reaction notes

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