Methanol → 5-Bromo-2-methoxypyridine
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH3:9][OH:10].[OH-].[K+]>CN(C=O)C>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:10][CH3:9])=[N:3][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a solution of 2,5-dibromopyridine (1.4 g, 5.9 mmol) in DMF (10 mL) was added MeOH (4 mL), and 8N aqueous KOH (1 mL). The solution was heated to 100° C. for 2 h, then cooled and partitioned between Et2O and H2O. The organic layer was washed with brine, dried over MgSO4 and concentrated to provide 840 mg of the title compound, which was used in the next step without further purification.
Workup
- temperaturecooled
- custompartitioned between Et2O and H2O
- washThe organic layer was washed with brine
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5763fc2c573e413aa07bf5759ce05d22
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922742
Reaction notes
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