HCID 59834277, compound → HCID 59834406, compound

HRID 230146Notes

Reaction equation

HRID 230146 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-2329f8bda1c947458da35f3779709693
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

Loading…