Ethyl Bromide → 2-Bromo-5-ethoxypyridine
Reaction equation
Br[CH2:2][CH3:3].C([O-])([O-])=O.[K+].[K+].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][N:12]=1>C(#N)C>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:2][CH3:3])=[CH:13][N:12]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2.51 g (22.99 mmol) 1-bromoethane and 1.99 g (14.37 mmol) K2CO3 are added to a mixture of 1.0 g (5.75 mmol) 2-bromo-5-hydroxypyridine in 100 mL ACN. The mixture is stirred at reflux over night. Then the reaction mixture is poured onto water and extracted with TBME. The organic layer is dried with Na2SO4 and the solvent is removed under vacuo. The residue is purified by column chromatography (silica gel, PE/EtOAC 1/1).
Workup
- temperatureat reflux over night
- additionThen the reaction mixture is poured onto water
- extractionextracted with TBME
- dry with materialThe organic layer is dried with Na2SO4
- customthe solvent is removed under vacuo
- customThe residue is purified by column chromatography (silica gel, PE/EtOAC 1/1)
Sources & evidence
- ORD record
- ord-36769e8c1de347da8d1796f0a24d3516
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835472B2
Reaction notes
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