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

HRID 127887Notes

Reaction equation

HRID 127887 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 354.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trichloroethyl pyruvate (3.7 g, 1.7 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-d3d5be830ce9495da8661c047a363561
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Reaction notes

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