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

HRID 473743Notes

Reaction equation

HRID 473743 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[N:6][C:7]=1[Cl:8].[C:10](=O)([O-])[O-].[K+].[K+].IC>C(#N)C.O>[Br:1][C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 145952265-Bromo-6-chloropyridin-3-ol

Product 1

HCID 467388143-Bromo-2-chloro-5-methoxypyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 5-bromo-6-chloropyridin-3-ol (2.95 g, 14.15 mmol) and potassium carbonate (1.28 mL, 21.23 mmol) in acetonitrile (45 mL) under a nitrogen atmosphere was added iodomethane (0.93 mL, 14.86 mmol). The reaction mixture was stirred at room temperature for 24 h. The reaction mixture was diluted with water and extracted with EtOAc (2×). The combined organic layers were washed with sat. sodium chloride, dried over magnesium sulfate, filtered, and concentrated. The resulting crude product was purified by silica gel chromatography to give 3-bromo-2-chloro-5-methoxypyridine. MS (ESI, pos. ion) m/z: 221.9 and 223.9 (M+1).

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic layers were washed with sat. sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-955f172ddda64ad9983685d692155e5b
Source dataset
uspto-grants-2014_01
Patent number
US08637500B2

Reaction notes

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