Methyl iodide → 2-Bromo-3-methoxypyridine

HRID 983411Notes

Reaction equation

HRID 983411 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].[CH3:11]I>C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH3:11])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 903642-Bromo-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-bromo-3-hydroxy-pyridine (1 equiv., Aldrich Chemical Company) in THF is treated with NaH (1 equiv.) at 0° C. for 30 min. Methyl iodide (1 equiv.) is added and stirred for 18 h. The reaction mixture is evaporated, the residue is taken into ethyl acetate, washed with 5% Na2CO3 (aqueous), dried over MgSO4 and evaporated to give 2-bromo-3-methoxy-pyridine.

Workup

  1. customThe reaction mixture is evaporated
  2. washwashed with 5% Na2CO3 (aqueous)
  3. dry with materialdried over MgSO4
  4. customevaporated

Sources & evidence

ORD record
ord-f08e819f122a4070a6e0fa75f783be95
Source dataset
uspto-grants-2005_03
Patent number
US06864267B2

Reaction notes

Loading…