Methyl iodide → 2-Methoxy-3-nitrobenzaldehyde

HRID 1179616Notes

Reaction equation

HRID 1179616 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-1c66ccb78c9b44c9bec7b4e7a71ace3a
Source dataset
uspto-grants-2007_10
Patent number
US07279481B2

Reaction notes

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