Methyl iodide → 2,6-Dichloro-3-methoxybenzaldehyde

HRID 2235209Notes

Reaction equation

HRID 2235209 reaction equation
[Cl:1][C:2]1[C:9]([OH:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5].[C:12](=O)([O-])[O-].[K+].[K+].C(=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[Cl:1][C:2]1[C:9]([O:10][CH3:12])=[CH:8][CH:7]=[C:6]([Cl:11])[C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 11430Potassium CarbonateHCID 104425302,6-Dichloro-3-hydroxy-benzaldehyde

Product 1

HCID 149271732,6-Dichloro-3-methoxybenzaldehydeYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Dissolve 2,6-dichloro-3-hydroxy-benzaldehyde (10.7 g, 56 mmol) in N,N-dimethylformamide (80 ml), add potassium carbonate (15 g, 112 mmol), cesium carbonate(18.3 g, 56 mmol), iodomethane (7 ml, 112 mmol) and stir over night at room temperature. Filter reaction mixture into water washing solids with DMF, extract filtrate with ethyl acetate wash with water, brine, dry over sodium sulfate, filter and concentrate to yield 10 g (87%) of 2,6-dichloro-3-methoxy-benzaldehyde.

Workup

  1. filtrationFilter
  2. customreaction mixture into water washing solids with DMF
  3. extractionextract filtrate with ethyl acetate
  4. washwash with water, brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-ecc07088962e4b55ae6edd2b1a9647b9
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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