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

HRID 2426065Notes

Reaction equation

HRID 2426065 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].CI.[C:14](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[F:1][C:2]1[CH:3]=[C:4]([Cl:11])[C:5]([O:10][CH3:14])=[C:6]([CH:9]=1)[CH:7]=[O:8]

Participants

6

Reactant 3

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

Product 1

HCID 130935603-Chloro-5-fluoro-2-methoxybenzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

5-Fluoro-2-hydroxy-3-chlorobenzaldehyde (2.0 g, 11.01 mmol) was dissolved in N,N-dimethylformamide (30 mL) and to the solution was added methyl iodide (1.1 mL, 18.11 mmol) and potassium carbonate (4.4 g, 30.21 mmol). The mixture was stirred at 100° C. for one hour, cooled to room temperature and then diluted with water (40 mL). After extraction twice with ethyl acetate (40 mL) the combined organic layer was washed with brine and then dried over Na2SO4. The solvent was removed and the solid residue was treated with methanol. After filtration and drying desired compound was obtained 2.0 g (99%). 1H NMR (400 MHz, CDCl3): δ 10.21 (s, 1H), 7.25 (dd, 1H), 7.12 (dd, 1H), 3.75 (s, 3H).

Workup

  1. temperaturecooled to room temperature
  2. extractionAfter extraction twice with ethyl acetate (40 mL) the combined organic layer
  3. washwas washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. additionthe solid residue was treated with methanol
  7. filtrationAfter filtration
  8. dry with materialdrying desired compound
  9. customwas obtained 2.0 g (99%)

Sources & evidence

ORD record
ord-dd75fb5ad7ce4ee98b585036bc35babf
Source dataset
uspto-grants-2011_06
Patent number
US07968538B2

Reaction notes

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