Ethyl 4-bromo-3-oxobutanoate → HCID 178472904, compound
Reaction equation
[N:1]([O-:3])=O.[Na+].[Br:5][CH2:6][C:7](=[O:14])[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10]>O.C(O)(=O)C>[OH:3][N:1]=[C:8]([C:7]([CH2:6][Br:5])=[O:14])[C:9]([O:11][CH2:12][CH3:13])=[O:10]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
A solution of sodium nitrite (12.4 g.) in water (150 ml.) was dropwise added with stirring at 5° to 7° C. to a solution of ethyl 4-bromoacetoacetate (30 g.) in acetic acid (200 ml.) and the mixture was stirred for 2 hours at 10° C. Water (200 ml.) was added to the reaction mixture and the resultant mixture was extracted with ether (500 ml.). The extract was washed twice with water (200 ml.) and with a sodium chloride aqueous solution (200 ml.) and dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give yellowish brown crystals of ethyl 2-hydroxyimino-4-bromoacetoacetate (a mixture of syn and anti isomers) (32.6 g.).
Workup
- extractionthe resultant mixture was extracted with ether (500 ml.)
- washThe extract was washed twice with water (200 ml.) and with a sodium chloride aqueous solution (200 ml.)
- dry with materialdried over magnesium sulfate
- distillationThe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-990cf06f94414fccab31ac80c749fdd0
- Source dataset
- uspto-grants-1985_01
- Patent number
- US04493833
Reaction notes
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