Methyl iodide → 2-Bromo-3-methoxypyridine

HRID 551758Notes

Reaction equation

HRID 551758 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([OH:10])=[CH:8][CH:7]=[CH:6][N:5]=1.I[CH3:12]>CN(C=O)C>[Br:3][C:4]1[C:9]([O:10][CH3:12])=[CH:8][CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Product 1

HCID 903642-Bromo-3-methoxypyridineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (5.91 g, 147.8 mmol) to a rapidly stirred solution of 2-bromo-3-pyridinol in DMF (anhydrous, 200 mL). After 30 minutes, add iodomethane (9.2 mL, 147.8 mmol) and stir under N2 for 2.5 hours. Quench with water and concentrate. Partition residue between Et2O) and water, separate layers. Extract from aqueous layer with Et2O (×2), dry combined layers over MgSO4 and concentrate. Purify residue by flash chromatography on silica gel eluting with 0-25% EtOAc/hexanes to afford 2-bromo-3-methoxy-pyridine (21.0 g, 83%).

Workup

  1. customQuench with water
  2. concentrationconcentrate
  3. customPartition residue between Et2O) and water, separate layers
  4. extractionExtract from aqueous layer with Et2O (×2)
  5. dry with materialdry combined layers over MgSO4
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-3e2e9165a2fb4e8a94bdfda89ce7a5bb
Source dataset
uspto-grants-2011_05
Patent number
US07947841B2

Reaction notes

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