Water → 2-Bromo-5-methoxypyridine

HRID 1966229Notes

Reaction equation

HRID 1966229 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.[H-].[Na+].I[CH3:12].O>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:12])=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 27628652-Bromo-5-hydroxypyridine

Product 1

HCID 111481512-Bromo-5-methoxypyridineYield 79%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromo-5-hydroxypyridine (5 mmol) is dissolved in DMF (10 ml) and NaH (1.4 eq., 60% suspension in liquid paraffin) is added. After 30 min iodomethane (2 eq.) is added and the reaction solution is stirred 3 days. The reaction solution is pored into water and extracted with methyl-tert.-butyl ether. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. 2-Bromo-5-methoxy-pyridine is obtained as yellow oil in a yield of 79%; HPLC (method C): 1.49 min; LC-MS (method A): 1.16 min, 187.95 (M+H+).

Workup

  1. extractionextracted with methyl-tert.-butyl ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-ab2b7acfc82a4f708952ca1a02ca7086
Source dataset
uspto-grants-2013_04
Patent number
US08420642B2

Reaction notes

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