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Potassium Carbonate → 3-Allyl-5-[(2-chloro-4-fluorophenoxy)methyl]-1,2,4-oxadiazole

HRID 4896
Notes
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Reaction equation

HRID 4896 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH2:10]([C:13]1[N:17]=[C:16]([CH2:18]Cl)[O:15][N:14]=1)[CH:11]=[CH2:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:10]([C:13]1[N:17]=[C:16]([CH2:18][O:9][C:3]2[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=2[Cl:1])[O:15][N:14]=1)[CH:11]=[CH2:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 748142-Chloro-4-fluorophenolHCID 197971305-(Chloromethyl)-3-(prop-2-en-1-yl)-1,2,4-oxadiazole

Product 1

HCID 197971293-Allyl-5-[(2-chloro-4-fluorophenoxy)methyl]-1,2,4-oxadiazoleYield 80.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.71 g of 2-chloro-4-fluorophenol, 0.77 g of 3-allyl-5-chloromethyl-1,2,4-oxadiazole and 0.83 of potassium carbonate were added to 20 ml of acetone. After completion of the reaction, the resulting precipitates were filtered out from the mixture and then acetone was removed by distillation, and the residue was purified by column chromatography (benzene:hexane=1:1) to obtain 1.05 g of the desired product(yield: 80.8%).

Workup

  1. customAfter completion of the reaction
  2. customthe resulting precipitates
  3. filtrationwere filtered out from the mixture
  4. customacetone was removed by distillation
  5. customthe residue was purified by column chromatography (benzene:hexane=1:1)

Sources & evidence

ORD record
ord-78085214e0d5496ab614bdad6a715709
Source dataset
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05242890

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes