Methanol → 3-Bromo-5-methoxypyridine

HRID 2416604Notes

Reaction equation

HRID 2416604 reaction equation
[Na].[CH3:2][OH:3].[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9](Br)[CH:10]=1.[OH-].[Na+]>CS(C)=O>[Br:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([O:3][CH3:2])[CH:10]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 693693,5-DibromopyridineHCID 5360545Sodium

Product 1

HCID 8171633-Bromo-5-methoxypyridine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
90 °C

Procedure

Sodium (2.33 g, 101.3 mmol) was added to methanol (50 ml) and was allowed to react, the mixture was evaporated. 3.5-Dibromopyridine (20.0 g, 84.4 mmol) and dimethyl sulfoxide (100 ml) were added. The mixture was stirred at 90° C. for 2 h. Sodium hydroxide (400 ml, 1 M) was added and the mixture was extracted twice with diethyl ether (200 ml). Chromatography on silica gel with dichloromethane and 3% ethanol as solvent gave the title compound. Yield 10.6 g, 67%. Mp 30-32° C.

Workup

  1. customto react
  2. customthe mixture was evaporated
  3. extractionthe mixture was extracted twice with diethyl ether (200 ml)

Sources & evidence

ORD record
ord-0ae6f493af944114847a2ad4d2fcb37d
Source dataset
uspto-grants-2004_11
Patent number
US06825189B1

Reaction notes

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