Triethylamine → 3-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole
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].C1C(=O)N(Cl)C(=O)C1.[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.CCN(CC)CC>CN(C=O)C.O>[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
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 40 °C
Procedure
A mixture of 4-bromo-3-methylbenzaldehyde oxime (384 mg, 0.5 mmol) and NCS (286.7 mg, 2.14 mmol) in DMF (10 mL) was stirred at 40° C. for 40 min. The mixture was cooled to 0° C. and to it was added 1,3-dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene (261 mg, 1.08 mmol) followed by Et3N (0.15 mL). The reaction mixture was stirred at rt for 20 h, poured into water and extracted with EA (10 mL). The organic layer was washed with water, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel to give 3-(4-bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (364.2 mg; yield 82%) as a white solid.
Workup
- temperatureThe mixture was cooled to 0° C. and to it
- stirringThe reaction mixture was stirred at rt for 20 h
- extractionextracted with EA (10 mL)
- washThe organic layer was washed with water
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography over silica gel
Sources & evidence
- ORD record
- ord-887b75dd17584603946ba8fbe1bb5380
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09156860B2
Reaction notes
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