Bromotrichloromethane → Malonic acid, bromoethyl-, diethyl ester

HRID 654606Notes

Reaction equation

HRID 654606 reaction equation
[CH2:1]([CH:3]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[Br:14]C(Cl)(Cl)Cl>O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)([O-])[O-].[K+].[K+]>[Br:14][C:3]([CH2:1][CH3:2])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

5

Reactant 2

HCID 6383BromotrichloromethaneHCID 8610Diethyl ethylmalonate

Product 1

HCID 141469Malonic acid, bromoethyl-, diethyl esterYield 95%

Reagents, catalysts & solvents 2

HCID 11430Potassium CarbonateCatalystHCID 11726816Tetrabutylammonium Fluoride TrihydrateCatalyst

Procedure

In a 10 mL round-bottom flask, 1.88 g of diethyl ethylmalonate (10 mmol), 2.18 g of bromotrichloromethane (11 mmol), 79 mg of tetra-n-butylammonium fluoride trihydrate (0.25 mmol), and 69 mg of potassium carbonate (0.5 mmol) were stirred at 24° C. for 1 h. An exothermic reaction caused the temperature of the mixture to rise to 40° C. After filtration of the solids, the solution was found to contain 2.5 g (95% yield) of diethyl α-bromo-α-ethylmalonate.

Workup

  1. customAn exothermic reaction
  2. customto rise to 40° C
  3. filtrationAfter filtration of the solids

Sources & evidence

ORD record
ord-c901fdc568f648ab94821a48eee83946
Source dataset
uspto-grants-1992_07
Patent number
US05132475

Reaction notes

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