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

HRID 216002Notes

Reaction equation

HRID 216002 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]=[N:7][OH:8])=[CH:4][C:3]=1[CH3:11].ClN1C(=O)CCC1=O.[Cl:20][C:21]1[CH:26]=[C:25]([C:27]([C:29]([F:32])([F:31])[F:30])=[CH2:28])[CH:24]=[C:23]([Cl:33])[CH:22]=1.C(N(CC)CC)C>CN(C)C=O.O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[CH2:28][C:27]([C:25]3[CH:24]=[C:23]([Cl:33])[CH:22]=[C:21]([Cl:20])[CH:26]=3)([C:29]([F:30])([F:32])[F:31])[O:8][N:7]=2)=[CH:4][C:3]=1[CH3:11]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 738479544-Bromo-3-methylbenzaldehyde oxime

Product 1

HCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazoleYield 64.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

4-Bromo-3-methyl-benzaldehyde oxime (1.3 g) (Example I2) and N-chloro-succinimide (“NCS”) (1.8 g) were dissolved in N,N-dimethylformamide (15 ml). The reaction mixture was stirred at ambient temperature for 90 minutes. A solution of 1,3-dichloro-5-(1-trifluoromethyl-vinyl)-benzene (1.3 g) (prepared according to WO 2005/085216) and triethylamine (1.9 ml) in N,N-dimethylformamide (15 ml) was added and the reaction mixture was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water and ethyl acetate and the phases were separated. The organic phase was washed twice with water and the aqueous phases were extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/dichloromethane 4:1) to give 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (1.57 g). 1H-NMR (400 MHz, CDCl3): 7.40 (m, 6H), 4.05 (d, 1H), 3.65 (d, 1H), 2.40 (s, 3H) ppm.

Workup

  1. stirringthe reaction mixture was stirred at ambient temperature for 18 hours
  2. customthe phases were separated
  3. washThe organic phase was washed twice with water
  4. extractionthe aqueous phases were extracted twice with ethyl acetate
  5. dry with materialThe combined organic phases were dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/dichloromethane 4:1)

Sources & evidence

ORD record
ord-acbf003de6a64896a4fba41cbd9da11e
Source dataset
uspto-grants-2012_06
Patent number
US08193221B2

Reaction notes

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