Dimethylformamide → Methyl[3-methoxy-5-(trifluoromethyl)phenyl]acetate

HRID 1686422Notes

Reaction equation

HRID 1686422 reaction equation
O[C:2]1[CH:3]=[C:4]([CH2:12]C(O)=O)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.I[CH3:17].[C:18](=[O:21])([O-])[O-:19].[K+].[K+].CN([CH:27]=[O:28])C>O>[CH3:17][O:19][C:18](=[O:21])[CH2:12][C:4]1[CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=[C:2]([O:28][CH3:27])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 690656243-Hydroxy-5-(trifluoromethyl)phenylacetic acid

Product 1

HCID 86625038Methyl[3-methoxy-5-(trifluoromethyl)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The product from example 25 step (iv) (1.0 g) was dissolved in dry DMF (10 ml) and treated with iodomethane (0.6 ml) and potassium carbonate (1.25 g). The mixture was stirred at room temperature overnight. The mixture was diluted with water, extracted with ether, dried (MgSO4) and evaporated under reduced pressure to give an oil. The oil was purified by flash column chromatography (eluent 2:1 diethylether/isohexane) (1.30 g).

Workup

  1. extractionextracted with ether
  2. dry with materialdried (MgSO4)
  3. customevaporated under reduced pressure
  4. customto give an oil
  5. customThe oil was purified by flash column chromatography (eluent 2:1 diethylether/isohexane) (1.30 g)

Sources & evidence

ORD record
ord-0e2c1b43e702403aabd185e5f0a4b31f
Source dataset
uspto-grants-2012_04
Patent number
US08148572B2

Reaction notes

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