2,2,2-Trifluoro-1-(2-fluoro-4-iodopyridin-3-yl)ethanol → 2,2,2-Trifluoro-1-(2-fluoro-4-iodopyridin-3-yl)ethanone

HRID 1920879Notes

Reaction equation

HRID 1920879 reaction equation
[F:1][C:2]([F:14])([F:13])[CH:3]([C:5]1[C:6]([F:12])=[N:7][CH:8]=[CH:9][C:10]=1[I:11])[OH:4]>C1(C)C=CC=CC=1.[O-2].[Mn+4].[O-2]>[F:14][C:2]([F:1])([F:13])[C:3]([C:5]1[C:6]([F:12])=[N:7][CH:8]=[CH:9][C:10]=1[I:11])=[O:4]

Participants

4

Reactant 1

HCID 579697722,2,2-Trifluoro-1-(2-fluoro-4-iodopyridin-3-yl)ethanol

Product 1

HCID 579695632,2,2-Trifluoro-1-(2-fluoro-4-iodopyridin-3-yl)ethanoneYield 89.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Procedure

2,2,2-trifluoro-1-(2-fluoro-4-iodo-3-pyridyl)ethanol (45 g, 140.2 mmol) was dissolved in anhydrous toluene (1 L). Manganese (IV) oxide (143.4 g, 1.402 mol) was added portionwise with rapid stirring. The mixture was heated to reflux for 3 hours and then allowed to cool and filtered through a plug of celite. The solid residues were washed with EtOAc and the filtrate was concentrated to a deep red oil which was slurried in petrol and then filtered to give a white solid impurity. The filtrate was concentrated to give the product as a red oil (40 g, 89% Yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 3 hours
  3. temperatureto cool
  4. filtrationfiltered through a plug of celite
  5. washThe solid residues were washed with EtOAc
  6. concentrationthe filtrate was concentrated to a deep red oil which
  7. filtrationfiltered
  8. customto give a white solid impurity
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-952b612b903e466dbd0061f47c3a945f
Source dataset
uspto-grants-2012_05
Patent number
US08173635B2

Reaction notes

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