Methyl acetoacetate → Methyl 4-bromo-3-oxobutanoate
Reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].[Br:9]Br>C(Cl)(Cl)(Cl)Cl>[Br:9][CH2:5][C:3](=[O:4])[CH2:2][C:1]([O:7][CH3:8])=[O:6]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To 150 ml of anhydrous carbon tetrachloride solution containing 116 g of methyl acetoacetate was added dropwise 51 ml of bromine at below 5° C. After the addition was finished the reaction mixture was stirred overnight, then the reaction mixture was poured into ice-water, washed with a diluted sodium carbonate aqueous solution five times, then with a saturated sodium chloride aqueous solution, and dried with anhydrous calcium chloride. The solvent was removed by evaporation to yield 170 g of methyl 4-bromoacetoacetate.
Workup
- additionAfter the addition
- washwashed with a diluted sodium carbonate aqueous solution five times
- dry with materialwith a saturated sodium chloride aqueous solution, and dried with anhydrous calcium chloride
- customThe solvent was removed by evaporation
Sources & evidence
- ORD record
- ord-e26b683022364437a7ef1ee93cf14407
- Source dataset
- uspto-grants-1992_08
- Patent number
- US05137889
Reaction notes
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