Water → Methyl 2-bromo-4-(trifluoromethyl)benzoate

HRID 39423Notes

Reaction equation

HRID 39423 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:15](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[CH3:15][O:5][C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:10][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 676052-Bromo-4-(trifluoromethyl)benzoic acid

Product 1

HCID 46311084Methyl 2-bromo-4-(trifluoromethyl)benzoateYield 83.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2 g (7.434 mmol) 2-bromo-4-trifluoromethyl-benzoic acid (CAS: 328-89-2) in 20 ml dimethylformamide under nitrogen at room temperature, was added 1.13 g (8.177 mmol) potassium carbonate and 557 ul (8.921 mmol) methyl iodide. The mixture was stirred overnight under nitrogen. The mixture was poured into water (300 ml). The aqueous layer was extracted with ethyl acetate (2×80 ml). The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%) to provide 1.75 g (83%) of the title compound as an orange oil.

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate (2×80 ml)
  2. dry with materialThe combined extracts were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude oil was purified on silica gel (eluent: heptane/ethyl acetate 0 to 10%)

Sources & evidence

ORD record
ord-6dcecaee0a6d4c4b9227802aed2de46c
Source dataset
uspto-grants-2013_09
Patent number
US08524909B2

Reaction notes

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