m-Chloroperbenzoic acid → HCID 13339624, compound

HRID 1632124Notes

Reaction equation

HRID 1632124 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8](=[CH2:14])[CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1.BrC1C=C(C(=C)CC(Cl)(Cl)Cl)C=C([O:31]C)N=1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2([CH2:9][C:10]([Cl:13])([Cl:12])[Cl:11])[CH2:14][O:31]2)[CH:5]=[C:4]([O:15][CH3:16])[N:3]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 13339622HCID 13339622, compoundHCID 13339623HCID 13339623, compound

Product 1

HCID 13339624HCID 13339624, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 11.8 g of 2-chloro-6-methoxy-4-(3,3,3-trichloro-1-methylenepropyl)pyridine containing the 2-bromo-6-methoxy-4-(3,3,3-trichloro-1-methylenepropyl)pyridine byproduct in 300 ml of chloroform was added 10.3 g of 85% m-chloro-perbenzoic acid. The solution was heated at reflux for 32 hours, cooled, and washed with 2N sodium hydroxide, water, and dried (Na2SO4). The solvent was removed in vacuo, leaving 12.5 g of crude product which was purified by high pressure liquid chromatography using 5% ethyl acetate in hexane as eluent. 5.4 g of pure product containing 16% of the bromo derivative was obtained. Analysis of the mixture was confirmed by gas-liquid chromatography, nuclear magnetic resonance spectroscopy, mass spectroscopy, and elemental analysis. Elemental analysis for the mixture:

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux for 32 hours
  3. temperaturecooled
  4. washwashed with 2N sodium hydroxide, water
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-33300e7ef29845e69c9b35cb38888fb6
Source dataset
uspto-grants-1984_10
Patent number
US04474602

Reaction notes

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