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

HRID 1786828Notes

Reaction equation

HRID 1786828 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-f8718f05b648440eb618696387ae2d6a
Source dataset
uspto-grants-2009_03
Patent number
US07507851B2

Reaction notes

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