Carbon Dioxide → 2,2,2-Trichloroethyl 3-bromo-2-oxopropanoate

HRID 1862869Notes

Reaction equation

HRID 1862869 reaction equation
[C:1]([O:6][CH2:7][C:8]([Cl:11])([Cl:10])[Cl:9])(=[O:5])[C:2]([CH3:4])=[O:3].[Br:12]Br.C(=O)=O>O>[Br:12][CH2:4][C:2](=[O:3])[C:1]([O:6][CH2:7][C:8]([Cl:9])([Cl:10])[Cl:11])=[O:5]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 24408BromineHCID 129644372,2,2-Trichloroethyl 2-oxopropanoate

Product 1

HCID 143497182,2,2-Trichloroethyl 3-bromo-2-oxopropanoateYield 35.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trichloroethyl pyruvate (3.7 g, 17 mmole) is heated to 65° and 1.1 ml (17 mmole) of bromine is added dropwise over 1 hour. A stream of carbon dioxide is passed through the reaction mixture during the addition to remove the HBr formed in the reaction. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The extract is dried over MgSO4, evaporated and distilled in vacuum to give 1.8 g of trichloroethyl bromopyruvate, bp 74°-77° (0.01 mm).

Workup

  1. customto remove the HBr
  2. customformed in the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe extract is dried over MgSO4
  5. customevaporated
  6. distillationdistilled in vacuum

Sources & evidence

ORD record
ord-936400cb750543c7b72239f4cd3ddc47
Source dataset
uspto-grants-1979_09
Patent number
US04166816

Reaction notes

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