Methyl iodide → 3-Chloro-5-fluoro-2-methoxybenzaldehyde

HRID 544330Notes

Reaction equation

HRID 544330 reaction equation
[Cl:1][C:2]1[C:3]([OH:11])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6].[C:12](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[C:3]([O:11][CH3:12])=[C:4]([CH:7]=[C:8]([F:10])[CH:9]=1)[CH:5]=[O:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 27827493-chloro-5-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 130935603-Chloro-5-fluoro-2-methoxybenzaldehydeYield 69.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-Chloro-5-fluoro-2-hydroxybenzaldehyde (2.5 g., 0.014 mole) was taken into 25 ml. of acetone. Potassium carbonate (2.48 g., 0.018 mole) and methyl iodide (2.55 g., 0.018 mole) were added in sequence and the mixture stirred for 16 hours at room temperature. The reaction mixture was filtered and the filtrate concentrated to an oil. The oil was partitioned between methylene chloride and water. The organic layer was washed in sequence with fresh water, 1N sodium hydroxide and brine, dried over anhydrous magnesium sulfate, and concentrated to yield 3-chloro-5-fluoro-2-methoxybenzaldehyde (1.83 g., 69%; m.p. 59°-62° C.).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated to an oil
  3. customThe oil was partitioned between methylene chloride and water
  4. washThe organic layer was washed in sequence with fresh water, 1N sodium hydroxide and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-52f1714cca264c849871f21ed2b35d29
Source dataset
uspto-grants-1984_05
Patent number
US04448971

Reaction notes

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