Methyl iodide → 3-Bromo-2-methoxy-5-methylpyridine

HRID 869903Notes

Reaction equation

HRID 869903 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]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178430683HCID 178430683, compound

Product 1

HCID 219527573-Bromo-2-methoxy-5-methylpyridine

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6344DichloromethaneSolvent

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

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. 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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