1-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanol → 1-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

HRID 545088Notes

Reaction equation

HRID 545088 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:13])[F:12])[C:5]([CH:8]([OH:10])[CH3:9])=[N:6][CH:7]=1>C1COCC1.O=[Mn]=O>[Br:1][C:2]1[CH:3]=[C:4]([C:11]([F:14])([F:12])[F:13])[C:5]([C:8](=[O:10])[CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 671904531-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanol

Product 1

HCID 586455621-(5-Bromo-3-(trifluoromethyl)pyridin-2-yl)ethanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 1-(5-bromo-3-(trifluoromethyl)pyridin-2-yl)ethanol (3.75 g, 0.01394 moles) in anhydrous THF (75 mL) and add MnO2 (12.1-24.2 g, 10 to 20 eq) at room temperature. Reflux the mixture under N2 atmosphere for 3 days. Cool the reaction mixture, filter through celite, wash the celite with THF (3×50 mL) and then concentrate under vacuum to afford the title compound as a colorless yellow oil.

Workup

  1. temperatureReflux the mixture under N2 atmosphere for 3 days
  2. temperatureCool the reaction mixture
  3. filtrationfilter through celite
  4. washwash the celite with THF (3×50 mL)
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-036b11ee2e62428190f8be08d951fb6f
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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