Bromine → 5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine

HRID 1844704Notes

Reaction equation

HRID 1844704 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CC([O-])=O.[Na+].[Br:17]Br>CC(O)=O>[Br:17][C:7]1[CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[C:4](=[O:9])[NH:5][CH:6]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 36784112(1H)-Pyridinone, 3-(trifluoromethyl)-

Product 1

HCID 134917805-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-(trifluoromethyl)pyridin-2(1H)-one (25.0 g, 0.15 mol) in AcOH (300 mL) were added NaOAc (15.1 g, 0.18 mol) and dropwise Br2 (8.6 mL, 0.17 mol). Then the mixture was stirred at 80° C. overnight, concentrated, diluted with sat aq. NaHCO3 and extracted with EtOAc twice. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=7/2) to give compound P45a (29.7 g, 80%) as a white solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with sat aq. NaHCO3
  3. extractionextracted with EtOAc twice
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (PE/EA=7/2)
  9. customto give compound P45a (29.7 g, 80%) as a white solid

Sources & evidence

ORD record
ord-4ef11352619d4c119d2ddfcb7a71b57f
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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