Bromine → 5-Bromo-2-hydroxy-3-(trifluoromethyl)pyridine
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]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- concentrationconcentrated
- additiondiluted with sat aq. NaHCO3
- extractionextracted with EtOAc twice
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- custompurified by CC (PE/EA=7/2)
- 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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