Thionyl Chloride → HCID 22221071, compound

HRID 1794323Notes

Reaction equation

HRID 1794323 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14]O)=[CH:12][O:11][N:10]=2)=[CH:5][CH:4]=1.S(Cl)([Cl:20])=O>>[Cl:20][CH2:14][C:13]1[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:17])([F:16])[F:1])=[CH:4][CH:5]=2)=[N:10][O:11][CH:12]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22221163HCID 22221163, compound

Product 1

HCID 22221071HCID 22221071, compoundYield 95%

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(4-trifluoromethylphenyl)-4-isoxazolylmethanol (6.00 g) and thionyl chloride (10.0 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-3-(4-trifluoromethylphenyl)isoxazole (6.16 g, yield 95%). The crystals were recrystallized from ethyl acetate-hexane. melting point: 84–85° 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-2a5c1d5d46c94e49885e5973f83659d4
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

Loading…