Ethyl bromoacetate → 1,2-Di-[(ethoxycarbonyl)methyl]pyridinium bromide
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[Br:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>>[Br-:13].[CH2:18]([O:17][C:15]([CH2:14][N+:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])=[O:16])[CH3:19]Participants
3
Procedure
A mixture of ethyl 2-pyridylacetate (6.0 g, 0.036 mole) and ethyl bromoacetate (4.4 ml, 0.038 mole) was allowed to stand at room temperature for 72 h, during which time the product gradually crystallised out. The mixture was treated with acetone (80 ml) to dissolve unreacted starting materials and then filtered. The solid collected was dried under vacuum to afford 1,2-di-[(ethoxycarbonyl)methyl]pyridinium bromide as a beige solid (3.53 g, 30%).
Workup
- customthe product gradually crystallised out
- additionThe mixture was treated with acetone (80 ml)
- dissolutionto dissolve unreacted starting materials