Methyl iodide → 3-Bromo-2-methoxy-5-methylpyridine
Reaction equation
[Br:1][C:2]1[C:3]([OH:9])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.I[CH3:11]>C(Cl)(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:3]([O:9][CH3:11])=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
3-Bromo-2-hydroxy-5-methylpyridine (5.012 g, 26.7 mmol), silver carbonate (9.58 g, 34.7 mmol), and iodomethane (5 mL, 80.0 mmol) were combined in CHCl3 (75 mL) and stirred at 55° C. for 3 hours. The mixture was cooled and filtered through Celite, and the filtrate was concentrated and purified by silica gel chromatography (0-100% EtOAc in hexanes) to give 3-bromo-2-methoxy-5-methyl-pyridine.
Workup
- temperatureThe mixture was cooled
- filtrationfiltered through Celite
- concentrationthe filtrate was concentrated
- custompurified by silica gel chromatography (0-100% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-3b4f135f3db4445382f3496dd8597d2c
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049015B2
Reaction notes
Loading…