Methyl iodide → 5-Fluoro-2-methoxybenzaldehyde

HRID 505603Notes

Reaction equation

HRID 505603 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].IC.[C:13](=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:13])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27373285-Fluorosalicylaldehyde

Product 1

HCID 27349435-Fluoro-2-methoxybenzaldehyde

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

20.0 g (0.143 mol) of 5-fluoro-2-hydroxybenzaldehyde are dissolved in 250 ml of acetonitrile. 81.04 g (0.57 mol) of iodomethane and 39.5 g (285 mol) of potassium carbonate are added, and the suspension is heated at reflux for 3 hours. The suspension is filtered and the mother liquor is diluted with ethyl acetate, washed twice with water, dried over magnesium sulphate and filtered, and the solvents are evaporated under reduced pressure.

Workup

  1. temperaturethe suspension is heated
  2. temperatureat reflux for 3 hours
  3. filtrationThe suspension is filtered
  4. additionthe mother liquor is diluted with ethyl acetate
  5. washwashed twice with water
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. customthe solvents are evaporated under reduced pressure

Sources & evidence

ORD record
ord-af62614a95ab488ca242ca5d15dc1fce
Source dataset
uspto-grants-2010_08
Patent number
US07781470B2

Reaction notes

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