Methyl iodide → 3-Fluoro-4,5-dimethoxybenzaldehyde

HRID 1354000Notes

Reaction equation

HRID 1354000 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].I[CH3:14]>CN(C=O)C>[F:1][C:2]1[CH:9]=[C:6]([CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH3:14])[CH:7]=[O:8]

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 6034473-Fluoro-4,5-dimethoxybenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution prepared from 100 mL of DMF and 5-fluorovanillin (lit 1.0 g, 5.88 mmol). After 15 minutes, iodomethane was added, and stirring at room temperature continued for 16 hours. The reaction was terminated by the addition of water, the mixture was extracted with hexane (3×100 ML), and solvents were removed in vacuo. Purification by flash chromatography on a column of silica gel using hexane-ethyl acetate (4:1) as eluent afforded a colorless solid (1 g, 93% yield); mp 51–53° C. (Lit17 mp 52–53° C.) 1H-NMR (300 MHz, CDCl3) δ 3.94 (s, 3H), 4.05 (s, 3H), 7.24 (s, 1H), 7.26 (s, 1H), 9.82 (s, 1H).

Workup

  1. waitcontinued for 16 hours
  2. customThe reaction was terminated by the addition of water
  3. extractionthe mixture was extracted with hexane (3×100 ML), and solvents
  4. customwere removed in vacuo
  5. customPurification by flash chromatography on a column of silica gel

Sources & evidence

ORD record
ord-9439d5c773334b219297df1e1560f16d
Source dataset
uspto-grants-2007_05
Patent number
US07223747B2

Reaction notes

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