Thionyl Chloride → 4-(Chloromethyl)-3-(4-chlorophenyl)-5-methylisoxazole

HRID 1794324Notes

Reaction equation

HRID 1794324 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([CH2:13]O)=[C:11]([CH3:15])[O:10][N:9]=2)=[CH:4][CH:3]=1.S(Cl)([Cl:18])=O>>[Cl:18][CH2:13][C:12]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[N:9][O:10][C:11]=1[CH3:15]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 15121509(3-(4-Chlorophenyl)-5-methylisoxazol-4-yl)methanol

Product 1

HCID 222210554-(Chloromethyl)-3-(4-chlorophenyl)-5-methylisoxazoleYield 91%

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(4-chlorophenyl)-5-methyl-4-isoxazolylmethanol (2.23 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-3-(4-chlorophenyl)-5-methylisoxazole (2.20 g, yield 91%). 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-1f7d8971d0f942f1b8ee0c8999f71ed7
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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