Methyl iodide → 2-Methoxy-3-nitrobenzaldehyde

HRID 2373634Notes

Reaction equation

HRID 2373634 reaction equation
[OH:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:13](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[CH3:13][O:1][C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 789342-Hydroxy-3-nitrobenzaldehyde

Product 1

HCID 140810742-Methoxy-3-nitrobenzaldehydeYield 72%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-hydroxy-3-nitrobenzaldehyde in DMF was added portionwise cesium carbonate (3 eq), followed by iodomethane (1.2 eq.). The solution was warmed to 60° C. for 2 hours, then cooled to room temperature and filtered. The filtrate was concentrated under vacuum and purified by column chromatography on SPE cartridge (Silica) using as eluent cyclohexane-ethyl acetate (8:2) to give the product in 72% yield.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated under vacuum
  4. custompurified by column chromatography on SPE cartridge (Silica)
  5. customto give the product in 72% yield

Sources & evidence

ORD record
ord-70ad36ef6f624a56aef66e6cb4e8dbe3
Source dataset
uspto-grants-2008_12
Patent number
US07459456B2

Reaction notes

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