Azobisisobutyronitrile → Ethyl 4-(bromomethyl)-2-methyl-1,3-oxazole-5-carboxylate
Reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=1.[Br:13]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:7][C:5]1[N:6]=[C:2]([CH3:1])[O:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]Participants
Conditions
- Temperature
- 80 °C
Procedure
10 mmol of ethyl 2,4-dimethyl-1,3-oxazole-5-carboxylate was dissolved in 30 ml of carbon tetrachloride, then 11 mmol of N-bromosuccinimide was gradually added with keeping the temperature at 20 to 30° C. After the end of the adding, 0.5 mmol of azobisiso butyronitrile was gradually added. Then stirring was continued for 30 minutes at a room temperature. The temperature was heated up to 80° C. to carry out the reaction for 3 hours. The reacted liquid was cooled down to a room temperature. A precipitated solid matter was eliminated by filtration. The filtrate was washed with 30 ml of water and the organic phase was separated and extracted and dried under sodium sulfate. Then the solvent was evaporated out, obtaining ethyl 4-(bromo methyl)-2-methyl-1,3-oxazole-5-carboxylate.
Workup
- customat 20 to 30° C
- customthe reaction for 3 hours
- temperatureThe reacted liquid was cooled down to a room temperature
- filtrationA precipitated solid matter was eliminated by filtration
- washThe filtrate was washed with 30 ml of water
- customthe organic phase was separated
- extractionextracted
- customdried under sodium sulfate
- customThen the solvent was evaporated out
Sources & evidence
- ORD record
- ord-4e26ba1db84a4a4baef0442674750818
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08779086B2
Reaction notes
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