Thionyl Chloride → 3-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole

HRID 585074Notes

Reaction equation

HRID 585074 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]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22064161{5-[4-(Trifluoromethyl)phenyl]isoxazol-3-yl}methan-1-ol

Product 1

HCID 220642603-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]isoxazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customSolvent was evaporated under reduced pressure
  4. customthe residue was purified by preparative thin layer chromatography
  5. washeluting with 30% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c13309e4d15e4250802c821fc9ed2cb1
Source dataset
uspto-grants-2005_08
Patent number
US06930111B2

Reaction notes

Loading…