Methanol → 3-Bromo-2-methoxy-5-nitropyridine

HRID 1620102Notes

Reaction equation

HRID 1620102 reaction equation
[CH3:1][O-:2].[Na+].CO.[Br:6][C:7]1[C:8](Cl)=[N:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1>O>[Br:6][C:7]1[C:8]([O:2][CH3:1])=[N:9][CH:10]=[C:11]([N+:13]([O-:15])=[O:14])[CH:12]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 2308893-Bromo-2-chloro-5-nitropyridineHCID 10942334Sodium Methoxide

Product 1

HCID 215844513-Bromo-2-methoxy-5-nitropyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sodium methoxide (28% methanol solution) (2 ml) was added to a methanol (2 ml) solution containing 3-bromo-2-chloro-5-nitropyridine (100 mg), followed by stirring at room temperature for 1 hour. Water was added to the reaction solution, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and a yellow solid of 3-bromo-2-methoxy-5-nitropyridine (96 mg) was thus obtained.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe resultant was washed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-06f9c9a52fc6457d8c66c3707e9dcc82
Source dataset
uspto-grants-2014_07
Patent number
US08772320B2

Reaction notes

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