Dimethylformamide → 2-(3-Bromoprop-1-en-2-yl)-6-chloropyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([CH2:10]Cl)=[CH2:9])[N:3]=1.[Br-:12].[K+].CC(=O)CC.CN(C)C=O>O>[Br:12][CH2:10][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[N:3]=1)=[CH2:9]Participants
6
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 1.0 g of 2-chloro-6-(1-chloromethylvinyl) pyridine, 2.0 g of potassium bromide, 5 ml of 2-butanone and 5 ml of N,N-dimethylformamide was stirred at 100° C. for 12 hours. After the reaction mixture was cooled to room temperature, water was added thereto to extract the mixture with ethyl acetate. The extract was subsequently washed with an aqueous solution of 10% sodium thiosulfate, water, saturated saline solution in that order, and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluted with n-hexane - ethyl acetate 25:1) to obtain 0.80 g of the objective compound.
Workup
- temperatureAfter the reaction mixture was cooled to room temperature
- extractionto extract the mixture with ethyl acetate
- washThe extract was subsequently washed with an aqueous solution of 10% sodium thiosulfate, water, saturated saline solution in that order
- dry with materialdried over anhydrous magnesium sulfate
- distillationAfter distilling off the solvent
- customthe residue was purified by silica gel column chromatography (eluted with n-hexane - ethyl acetate 25:1)
Sources & evidence
- ORD record
- ord-292ba696cfe04055801b9bb659f5a4f7
- Source dataset
- uspto-grants-1990_10
- Patent number
- US04960897
Reaction notes
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