Methyl acetoacetate → Methyl 4-bromo-3-oxobutanoate

HRID 846632Notes

Reaction equation

HRID 846632 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

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

  1. additionAfter the addition
  2. washwashed with a diluted sodium carbonate aqueous solution five times
  3. dry with materialwith a saturated sodium chloride aqueous solution, and dried with anhydrous calcium chloride
  4. 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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