Chloroform → 5-bromo-1-methyl-1H-imidazole-4-carbaldehyde
Reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([CH:7]=[O:8])[N:4]=[CH:3]1.[Br:9]N1C(=O)CCC1=O.C(Cl)(Cl)Cl>C(=O)([O-])[O-].[Na+].[Na+]>[Br:9][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[CH:7]=[O:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of 1-methyl-1H-imidazole-4-carbaldehyde (0.50 g), N-bromosuccinimide (0.89 g) and chloroform (7.0 mL) was heated at reflux for 2 hours. The mixture was cooled to 0° C., diluted with saturated aqueous sodium carbonate solution (10 mL) and extracted with dichloromethane. The combined organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with a mixture of ethyl acetate and dichloromethane (0:1 to 7:10 by volume) to afford the title compound as a white solid (0.37 g).
Workup
- temperaturewas heated
- temperatureat reflux for 2 hours
- extractionextracted with dichloromethane
- extractionThe combined organic extract
- dry with materialwas dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
- customThe residue was purified by column chromatography on silica gel
- washeluting with a mixture of ethyl acetate and dichloromethane (0:1 to 7:10 by volume)
Sources & evidence
- ORD record
- ord-a32448b1735f42999ef93c7cc6231c28
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394836B2
Reaction notes
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