Water → 5-(3,5-Dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole

HRID 910385Notes

Reaction equation

HRID 910385 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.Cl[C:16](=[N:27][OH:28])[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([CH3:26])[CH:18]=1.C(=O)([O-])[OH:30].[K+].O>O1CCCC1>[CH:17]([O:30][CH:9]([CH3:10])[CH3:11])([CH3:22])[CH3:16].[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:11]([F:14])([F:12])[F:13])[O:28][N:27]=[C:16]([C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[C:19]([CH3:26])[CH:18]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516893Potassium BicarbonateHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 86611477alpha-Chloro-3-methyl-4-nitrobenzaldoxime

Product 2

HCID 7914Diisopropyl EtherHCID 231598015-(3,5-Dichlorophenyl)-3-(3-methyl-4-nitrophenyl)-5-trifluoromethyl-4,5-dihydroisoxazoleYield 113.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In a solution of 1.31 g of 3,5-dichloro-1-(1-trifluoromethylethenyl)benzene synthesized in Step 1 of Synthetic Example 3 and 1.17 g of α-chloro-3-methyl-4-nitrobenzaldoxime in 10 ml of tetrahydrofuran, 1.15 g of potassium hydrogen carbonate and 1.50 g of water were added, and stirred at room temperature for 18 hours. After the completion of the reaction, tetrahydrofuran was removed from the reaction mixture, 3 ml of water was added, and stirred under colloing with ice for further 30 minutes. Precipitated crystal was filtered off, washed with 5 ml of water and then 5 ml of diisopropyl ether to obtain 1.29 g of the aimed product as white crystal.

Workup

  1. customwas removed from the reaction mixture, 3 ml of water
  2. additionwas added
  3. stirringstirred
  4. waitunder colloing with ice for further 30 minutes
  5. customPrecipitated crystal
  6. filtrationwas filtered off
  7. washwashed with 5 ml of water

Sources & evidence

ORD record
ord-2ad9dd995d8945f09d0fb421afef1b6e
Source dataset
uspto-grants-2011_09
Patent number
US08022089B2

Reaction notes

Loading…