Potassium Carbonate → 3-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehyde

HRID 2399411Notes

Reaction equation

HRID 2399411 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12])[CH:5]=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][CH:22]1[CH2:24][CH2:23]1>CN(C)C=O>[CH:22]1([CH2:21][O:1][C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=2[O:10][CH:11]([F:12])[F:13])[CH:5]=[O:6])[CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 189736983-(Cyclopropylmethoxy)-4-(difluoromethoxy)benzaldehydeYield 104.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 3-hydroxy-4-difluoromethoxybenzaldehyde (19.55 g, 104 mmol) and potassium carbonate (21.56 g, 156 mmol) in dimethylformamide (150 mL) under an argon atmosphere at 60° C. was added bromomethylcyclopropane (15.13 mL, 156 mmol) and the mixture was stirred and heated at 65° C. After 1.5 h, the mixture was allowed to cool and was filtered. The filtrate was concentrated under reduced pressure and the residue was partitioned between ethylacetate and water and was extracted four times with ethyl acetate. The organic extract was washed twice with water and was dried (sodium sulfate). The solvent was removed in vacuo to provide an oil (26.4 g).

Workup

  1. temperatureto cool
  2. filtrationwas filtered
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was partitioned between ethylacetate and water
  5. extractionwas extracted four times with ethyl acetate
  6. extractionThe organic extract
  7. washwas washed twice with water
  8. dry with materialwas dried (sodium sulfate)
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a33123cc5891432a830524aa6fa390d9
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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