Methyl iodide → 3-Bromo-5-fluoro-2-methoxypyridine

HRID 1631301Notes

Reaction equation

HRID 1631301 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][CH:5]=[C:6]([F:8])[CH:7]=1.I[CH3:11]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([O:9][CH3:11])=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 407869053-Bromo-5-fluoropyridin-2-ol

Product 1

HCID 404270063-Bromo-5-fluoro-2-methoxypyridineYield 43.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Bromo-5-fluoropyridin-2(1H)-one (10.0 g, 52.1 mmol) and Ag2CO3 (10.0 g, 36.5 mmol) were combined in toluene (100 mL) and iodomethane (3.89 mL, 62.5 mmol) was added drop-wise. The reaction was stirred at ambient temperature overnight, filtered through Celite and the solids were washed with toluene. The filtrate was concentrated and the residue was purified on a silica gel column (5-25% EtOAc/hexanes) to afford 3-bromo-5-fluoro-2-methoxypyridine (4.70 g, 43.8%) as a clear oil.

Workup

  1. filtrationfiltered through Celite
  2. washthe solids were washed with toluene
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified on a silica gel column (5-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-70c7018b480a440c92ceb63b4c8426c6
Source dataset
uspto-grants-2014_07
Patent number
US08791123B2

Reaction notes

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