Potassium Bicarbonate → 3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

HRID 910391Notes

Reaction equation

HRID 910391 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:11]([F:14])([F:13])[F:12])=[CH2:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Br:15][C:16]1[CH:25]=[CH:24][C:19]([C:20](Cl)=[N:21][OH:22])=[CH:18][C:17]=1[CH3:26].C(=O)([O-])O.[K+]>O1CCCC1>[Br:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]2[CH2:10][C:9]([C:4]3[CH:3]=[C:2]([Cl:1])[CH:7]=[C:6]([Cl:8])[CH:5]=3)([C:11]([F:14])([F:12])[F:13])[O:22][N:21]=2)=[CH:18][C:17]=1[CH3:26]

Participants

5

Reactant 3

HCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 866114784-Bromo-alpha-chloro-3-methylbenzaldoxime

Product 1

HCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleYield 90.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a solution of 22.7 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene produced in Step 1 of Synthetic Example 3 and 26.0 g of 4-bromo-α-chloro-3-methylbenzaldoxime in 120 ml of tetrahydrofuran, 15.7 g of potassium hydrogen carbonate was added, and stirred under reflux with heat for 5 hours. After the completion of the reaction, the reaction mixture was left and cooled to room temperature, insoluble material was filtered off, then the solvent was distilled off under reduced pressure. 150 ml of water was added in the residue, stirred at room temperature for 18 hours, and precipitated crystal was filtered off and dried to obtain 38.6 g of the aimed product as white crystal.

Workup

  1. temperatureunder reflux
  2. temperaturewith heat for 5 hours
  3. customAfter the completion of the reaction
  4. waitthe reaction mixture was left
  5. filtrationinsoluble material was filtered off
  6. distillationthe solvent was distilled off under reduced pressure
  7. addition150 ml of water was added in the residue
  8. stirringstirred at room temperature for 18 hours
  9. customprecipitated crystal
  10. filtrationwas filtered off
  11. customdried

Sources & evidence

ORD record
ord-f8eb90539cb448828a83e35c9c609d32
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

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