Thionyl Chloride → HCID 22221286, compound

HRID 1794329Notes

Reaction equation

HRID 1794329 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[O:13][N:12]=[CH:11][C:10]=1[CH2:14]O.S(Cl)([Cl:18])=O>C1(C)C=CC=CC=1>[Cl:18][CH2:14][C:10]1[CH:11]=[N:12][O:13][C:9]=1[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22221119HCID 22221119, compound

Product 1

HCID 22221286HCID 22221286, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5-(2,4-difluorophenyl)-4-isoxazolylmethanol (2.50 g) in toluene (50 ml) was added dropwise thionyl chloride (2.11 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. 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 residue was subjected to silica gel column chromatography, and 4-chloromethyl-5-(2,4-difluorophenyl)isoxazole (2.20 g, yield 81%) was obtained as an oil from a fraction eluted with ethyl acetate-hexane (1:5, volume ratio). NMR (CDCl3) δ: 4.53 (2H, s), 6.95–7.15 (2H, m), 7.6–7.75 (1H, m), 8.43 (1H, s).

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

Sources & evidence

ORD record
ord-aa275bb5fd40409caa6cdb316732db7b
Source dataset
uspto-grants-2006_04
Patent number
US07022725B2

Reaction notes

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