Bromine → 3-Bromo-5-(trifluoromethyl)pyridin-2(1H)-one
Reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](=[O:9])[NH:7][CH:8]=1.C([O-])(=O)C.[Na+].[Br:17]Br>C(O)(=O)C>[Br:17][C:5]1[C:6](=[O:9])[NH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To 5-trifluoromethyl-2(1H)-pyridone (10.0 g, 61.3 mmol) and sodium acetate (5.25 g, 64 mmol) in acetic acid (100 ml) was added bromine (3.3 ml, 63 mmol) and the solution stirred at 80° C. for 2 hrs. After concentration in vacuo, the residue was suspended in saturated sodium bicarbonate solution (500 ml) and extracted with ethyl acetate (2×50 ml). The extracts were dried (MgSO4) and concentrated to give the product as a tan solid (14.22 g, 58.8 mmol, 96% yield).
Workup
- concentrationAfter concentration in vacuo
- extractionextracted with ethyl acetate (2×50 ml)
- dry with materialThe extracts were dried (MgSO4)
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-f6409a38a1f34f679fc1f343aed63f07
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225320B1
Reaction notes
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