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]>ClCCl.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
Procedure
To 3-bromo-5-methylpyridin-2-ol (500 mg, 2.7 mmol) and silver carbonate (2.6 g, 9.6 mmol) suspended in dichloromethane (10 mL) was added iodomethane (0.83 mL, 13 mmol). The reaction mixture was allowed to stir at room temperature overnight. The reaction mixture was filtered through a pad of celite and the volatiles were evaporated to yield 3-bromo-2-methoxy-5-methylpyridine, which was used directly in the next step. ESI-MS m/z calc. 201.0. found 202.3 (M+1)+. Retention time 1.51 minutes.
Workup
- filtrationThe reaction mixture was filtered through a pad of celite
- customthe volatiles were evaporated
Sources & evidence
- ORD record
- ord-87d2fd7b94f141d89814918cb66633fe
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969386B2
Reaction notes
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