HCID 59834277, compound → HCID 59834406, compound

HRID 271075Notes

Reaction equation

HRID 271075 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:10]1[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=1)[OH:9]>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:10]1[C:11]([Cl:17])=[N:12][C:13]([Cl:16])=[CH:14][CH:15]=1)=[O:9]

Participants

4

Reactant 1

HCID 59834277HCID 59834277, compound

Product 1

HCID 59834406HCID 59834406, compoundYield 115.9%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

(2-Chloro-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanol (12.2 g, 42.3 mmol) was dissolved in 200 mL of dry toluene, and 87 g of manganese dioxide was added. The reaction mixture was refluxed for 2.5 hours, and was then hot filtered through Celite. The Celite plug was washed with 80 mL of hot EtOAc (in several portions), and the organic solvents were combined. Removal of solvent under reduced pressure yielded 14.05 g of (2-chloro-phenyl)-(2,6-dichloro-pyridin-3-yl)-methanone as a viscous yellow oil. Mass Spec. M+H=288.

Workup

  1. temperatureThe reaction mixture was refluxed for 2.5 hours
  2. filtrationwas then hot filtered through Celite
  3. washThe Celite plug was washed with 80 mL of hot EtOAc (in several portions)
  4. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-c850f75894e442c2ba339e2f37e98f5b
Source dataset
uspto-grants-2008_11
Patent number
US07452880B2

Reaction notes

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