Methyl iodide → 3-Bromo-2-methoxy-5-(trifluoromethyl)pyridine

HRID 1976062Notes

Reaction equation

HRID 1976062 reaction equation
[Br:1][C:2]1[C:3](=[O:12])[NH:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.I[CH3:14]>CCCCCC.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:3]([O:12][CH3:14])=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 134917753-Bromo-5-(trifluoromethyl)pyridin-2(1H)-one

Product 1

HCID 148370183-Bromo-2-methoxy-5-(trifluoromethyl)pyridineYield 42.3%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 8058HexaneSolvent

Procedure

To a suspension of 3-bromo-5-trifluoromethyl-2(1H)-pyridone (2.0 g, 8.26 mmol) and silver carbonate (2.32 g, 8.4 mmol) in hexane (50 mL) was added iodomethane (1.05 mL, 16.8 mmol) and the resulting mixture heated at reflux for 16 hrs. The suspension was cooled, and filtered, and the filtrate concentrated in vacuo. The residue was purified by silica chromatography to give the product as an oil (893 mg, 3.49 mmol, 42% yield).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 16 hrs
  3. temperatureThe suspension was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated in vacuo
  6. customThe residue was purified by silica chromatography

Sources & evidence

ORD record
ord-c5a4f12b6a39499ebe806ee620d01bdf
Source dataset
uspto-grants-2001_05
Patent number
US06225320B1

Reaction notes

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