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