Sodium Iodide → 2-Chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)benzaldehyde

HRID 2251329Notes

Reaction equation

HRID 2251329 reaction equation
Cl[CH2:2][C:3]1[C:4]([C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:18])=[N:5][O:6][C:7]=1[CH:8]([CH3:10])[CH3:9].[Cl:19][C:20]1[CH:27]=[C:26]([OH:28])[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[Cl:19][C:20]1[CH:27]=[C:26]([O:28][CH2:2][C:3]2[C:4]([C:11]3[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:12]=3[Cl:18])=[N:5][O:6][C:7]=2[CH:8]([CH3:10])[CH3:9])[CH:25]=[CH:24][C:21]=1[CH:22]=[O:23]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 1853632-Chloro-4-hydroxybenzaldehydeHCID 592648754-(Chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole

Product 1

HCID 105263872-Chloro-4-((3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl)methoxy)benzaldehyde

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-isopropylisoxazole (1 g, 3.28 mmol), 2-chloro-4-hydroxybenzaldehyde (498 mg, 3.18 mmol), potassium carbonate (431 mg, 3.12 mmol), sodium iodide (98 mg, 0.66 mmol) in acetone (20 mL) was refluxed for 5 h. The reaction was concentrated and the residue was partitioned with ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and condensed to a residue which was chromatographed on silica gel eluting with 200% ethyl acetate/hexanes. Yield=0.98 g (71%) of 2-chloro-4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-benzaldehyde.

Workup

  1. temperaturewas refluxed for 5 h
  2. concentrationThe reaction was concentrated
  3. customthe residue was partitioned with ethyl acetate and water
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customcondensed to a residue which
  8. customwas chromatographed on silica gel eluting with 200% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-ab2acabe39a84e95ace825ae84137398
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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