Thionyl Chloride → 3-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole
Reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14]O)[CH:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:20])=O>ClCCl>[Cl:20][CH2:14][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)[O:13][N:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
{5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol (200 mg) was dissolved in dry dichloromethane (10 ml), and cooled to 0° C. The solution was stirred while adding a solution of thionyl chloride (2.74 ml) in dichloromethane (25 ml), then allowed to warm to room temperature and stirred overnight. Solvent was evaporated under reduced pressure, and the residue was purified by preparative thin layer chromatography, eluting with 30% ethyl acetate/hexane, to afford 3-(chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole, a compound of formula (25).
Workup
- temperatureto warm to room temperature
- stirringstirred overnight
- customSolvent was evaporated under reduced pressure
- customthe residue was purified by preparative thin layer chromatography
- washeluting with 30% ethyl acetate/hexane
Sources & evidence
- ORD record
- ord-168c147ecafd43ec8343a9396a8fcdce
- Source dataset
- uspto-grants-2006_06
- Patent number
- US07056924B2
Reaction notes
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