Bromocyclopentane → 3-(Cyclopentyloxy)-4-(difluoromethoxy)benzaldehyde

HRID 2399408Notes

Reaction equation

HRID 2399408 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[CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>CN(C)C=O>[CH:21]1([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])[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 27582954-(Difluoromethoxy)-3-hydroxybenzaldehyde

Product 1

HCID 177501163-(Cyclopentyloxy)-4-(difluoromethoxy)benzaldehydeYield 91.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 3-hydroxy-4-difluoromethoxybenzaldehyde 2.9 g, 15 mmol) and powdered potassium carbonate (3.2 g, 23 mmol) in dimethylformamide (15 mL) under an argon atmosphere was added bromocyclopentane (2.5 mL, 23 mmol) and the mixture was stirred and heated at 50° C. for 1 h and at 80°-85° C. 1.5 h. The mixture was allowed to cool and was partitioned between ethyl acetate and water. The organic extract was washed three times with water, was dried (sodium sulfate) and the solvent was removed in vacuo. Purification by flash chromatography, eluting with 20-30% ether/hexanes, provided a yellow solid (3.5 g, 89%).

Workup

  1. custom1.5 h
  2. temperatureto cool
  3. customwas partitioned between ethyl acetate and water
  4. extractionThe organic extract
  5. washwas washed three times with water
  6. dry with materialwas dried (sodium sulfate)
  7. customthe solvent was removed in vacuo
  8. customPurification by flash chromatography
  9. washeluting with 20-30% ether/hexanes

Sources & evidence

ORD record
ord-c7c7eecdb00149e28391f3a67980c4ef
Source dataset
uspto-grants-1995_09
Patent number
US05449686

Reaction notes

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