Hydrogen Bromide → Diethyl bromomalonate

HRID 991953Notes

Reaction equation

HRID 991953 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[Br:12]Br.Br>C(Cl)(Cl)(Cl)Cl>[Br:12][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 7761Diethyl MalonateHCID 24408Bromine

Product 1

HCID 69637Diethyl bromomalonateYield 80%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

16.0 g of diethyl malonate was added to 27.3 g of carbon tetrachloride. Into the resultant mixture was dropped 16.4 g of bromine under stirring at room temperature. After the completion of the dropping, the mixture was heated to 80° C. and refluxed for 1 hour to thereby remove hydrogen bromide formed by the reaction. The liquid reaction mixture thus obtained was washed with a 5% aqueous solution of sodium carbonate and carbon tetrachloride was distilled off. Then distillation was carried out to give 19.1 g (yield: 80.0%) of diethyl bromomalonate.

Workup

  1. temperatureAfter the completion of the dropping, the mixture was heated to 80° C.
  2. customformed by the reaction
  3. customThe liquid reaction mixture
  4. customthus obtained
  5. washwas washed with a 5% aqueous solution of sodium carbonate and carbon tetrachloride
  6. distillationwas distilled off
  7. distillationThen distillation

Sources & evidence

ORD record
ord-79bd1f0b669a4d148945b16dd4b05154
Source dataset
uspto-grants-2002_10
Patent number
US06465676B2

Reaction notes

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