Methanol → 2-Bromo-3-methoxypyridine

HRID 748740Notes

Reaction equation

HRID 748740 reaction equation
[H-].[Na+].[CH3:3]O.[Br:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][N:7]=1.CI>CN(C)C=O>[Br:5][C:6]1[C:11]([O:12][CH3:3])=[CH:10][CH:9]=[CH:8][N:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydride

Product 1

HCID 903642-Bromo-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under a nitrogen atmosphere, 60% oil sodium hydride (605 mg, 15.1 mmol) was added in portions to methanol (10 ml) under ice cooling. Twenty minutes later, a dimethylformamide (20 ml) solution of 2-bromo-3-hydroxypyridine (2.5 g, 14.4 mmol) was added to the resulting mixture. The reaction mixture was distilled under reduced pressure to remove methanol and to the residue was added methyl iodide (0.94 ml, 15.1 mmol). The mixture was stirred at room temperature for 3 hours.

Workup

  1. distillationThe reaction mixture was distilled under reduced pressure
  2. customto remove methanol

Sources & evidence

ORD record
ord-b3b0d6c6427645feb592134ba27e9b26
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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