Phenol → HCID 20032362, compound

HRID 231434Notes

Reaction equation

HRID 231434 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8]Br)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CC(C)=O>[Cl:1][C:2]1[C:7]([CH2:8][O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:6][C:5]([N:10]2[C:14](=[O:15])[C:13]3[CH2:16][CH2:17][CH2:18][CH2:19][C:12]=3[C:11]2=[O:20])=[C:4]([F:21])[CH:3]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 11430Potassium CarbonateHCID 20032357HCID 20032357, compound

Product 1

HCID 20032362HCID 20032362, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a mixture of 0.6 g (0.0016 mole) of N-(4-chloro-2-fluoro-5-bromomethylphenyl)-3,4,5,6-tetrahydrophthalimide and 0.22 g (0.0016 mole) of potassium carbonate in acetone was added 0.15 g (0.0016 mole) of phenol. The mixture was stirred overnight at room temperature and then was heated at 50° C. for approximately 24 hours. The reaction mixture was filtered, and the filter cake was washed with ethyl acetate. The filtrate was washed with water, dried, and the solvent was evaporated under reduced pressure, leaving a residue weighing 0.7 g. Preparative thin layer chromatography was used to separate the components of this residue, eluting with ethyl acetate/heptane (3/7). The product, 0.18 g of N-(4-chloro-2-fluoro-5-phenoxymethylphenyl)-3,4,5,6-tetrahydrophthalimide, was isolated as an oil. The nmr and ir were consistent with the proposed structure.

Workup

  1. temperaturewas heated at 50° C. for approximately 24 hours
  2. filtrationThe reaction mixture was filtered
  3. washthe filter cake was washed with ethyl acetate
  4. washThe filtrate was washed with water
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customleaving a residue
  8. customto separate the components of this residue
  9. washeluting with ethyl acetate/heptane (3/7)

Sources & evidence

ORD record
ord-b2745ee5e56c4163936a00748628a6e9
Source dataset
uspto-grants-1989_07
Patent number
US04846882

Reaction notes

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