Methyl iodide → 3-Iodo-2-methoxybenzaldehyde

HRID 1404366Notes

Reaction equation

HRID 1404366 reaction equation
[I:1][C:2]1[C:3]([OH:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6].[C:11](=O)([O-])[O-].[Cs+].[Cs+].CI>CC(N(C)C)=O.CCOCC>[I:1][C:2]1[C:3]([O:10][CH3:11])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[O:6]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 152099202-Hydroxy-3-iodobenzaldehyde

Product 1

HCID 108014193-Iodo-2-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 3-iodo-2-hydroxy-benzaldehyde (4.0 g, 16.06 mmol) in DMA (32 mL) was added cesium carbonate (5.85 g, 18 mmol) followed by methyl iodide (1.12 mL, 18 mmol). The resulting mixture was stirred for 4.75 hours then diluted with ether, washed with water, dried over magnesium sulfate and concentrated. The residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes) to give the title compound as an oil.

Workup

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica chromatography (50 g silica; eluted with 0-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-cae7c0572d9d4347ac38b10b26c20233
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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