Trifluoroacetic anhydride → 5-Bromo-2-methylpyridin-1-ium-1-olate
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N:6][CH:7]=1.OO.NC(N)=[O:13].FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[N+:6]([O-:13])[CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 5-bromo-2-methylpyridine (1 g, 5.81 mmol) and urea hydrogen peroxide (1.1 g, 12.2 mmol) in DCM (30 mL) at 0° C. was added trifluoroacetic anhydride (1.6 mL, 11.6 mmol). After warming to 25° C. over 12 h, the solution was partitioned between H2O-DCM. The aqueous phase was washed several times with DCM and the combined organic fractions were dried over Na2SO4, concentrated and purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (660 mg, 60%) as a white solid: LCMS (ES) m/z=190 (M+H)+.
Workup
- customthe solution was partitioned between H2O-DCM
- washThe aqueous phase was washed several times with DCM
- dry with materialthe combined organic fractions were dried over Na2SO4
- concentrationconcentrated
- custompurified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH))
Sources & evidence
- ORD record
- ord-5a4002a6501a4d3285946c69f2f172cf
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08338434B2
Reaction notes
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