Ethyl Acetate → 5-Bromo-2-(methylsulfinyl)pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.C(OCC)(=[O:12])C>O.C(O)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH3:9])=[O:12])=[N:6][CH:7]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
NalO4 (0.52 g) dissolved in water (0.5 mL) was added to a solution of 5-bromo-2-methylsulfanyl-pyridine (0.25 g) in acetic acid (3 mL) at room temperature. The resulting mixture was stirred at room temperature overnight. Then, water and ethyl acetate were added and the mixture was stirred for another 10 min. The organic phase was separated and washed with 10% aqueous Na2S2O3 solution, 10% aqueous K2CO3 solution, and brine. After drying (MgSO4), the solvent was evaporated to afford the title compound. Yield: 0.20 g (72% of theory); Mass spectrum (ESI+): m/z=220/222 (Br) [M+H]+.
Workup
- stirringthe mixture was stirred for another 10 min
- customThe organic phase was separated
- washwashed with 10% aqueous Na2S2O3 solution, 10% aqueous K2CO3 solution, and brine
- dry with materialAfter drying (MgSO4)
- customthe solvent was evaporated
Sources & evidence
- ORD record
- ord-deb7fa39ccb74c9b86cd34a40cf2f002
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08569292B2
Reaction notes
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