Thionyl Chloride → HCID 22220975, compound

HRID 1794325Notes

Reaction equation

HRID 1794325 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:3]=1[CH2:17]O.S(Cl)([Cl:21])=O>>[Cl:21][CH2:17][C:3]1[C:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)=[N:5][O:6][C:2]=1[CH3:1]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22221056HCID 22221056, compound

Product 1

HCID 22220975HCID 22220975, compoundYield 80%

Conditions

Temperature
0 °C

Procedure

A mixture of 5-methyl-3-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (1.75 g) and thionyl chloride (5.0 ml) was stirred at 0° C. for 30 min. The reaction mixture was concentrated, saturated aqueous sodium hydrogencarbonate was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained colorless crystals were filtrated to give 4-chloromethyl-5-methyl-3-(4-trifluoromethylphenyl)isoxazole (1.50 g, yield 80%). The crystals were recrystallized from diisopropyl ether. melting point: 91–92° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionsaturated aqueous sodium hydrogencarbonate was added to the residue
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. filtrationThe obtained colorless crystals were filtrated

Sources & evidence

ORD record
ord-941f43ebb0214d13a815dd0d534a1da9
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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