Ethyl benzoylacetate → ethyl 2-bromo-3-oxo-3-phenylpropanoate

HRID 1682562Notes

Reaction equation

HRID 1682562 reaction equation
[CH3:1][CH2:2][O:3][C:4]([CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:8])=[O:5].[Br:15]Br>C(Cl)(Cl)(Cl)Cl>[C:7]([CH:6]([Br:15])[C:4]([O:3][CH2:2][CH3:1])=[O:5])(=[O:8])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 7170Ethyl benzoylacetateHCID 24408Bromine

Product 1

HCID 237819ethyl 2-bromo-3-oxo-3-phenylpropanoate

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

25 ml (0.144 mol) of ethyl benzoyl acetate are dissolved in 50 ml of CCl4, 8.5 ml of bromine are added dropwise at 5° C. and the brown solution is stirred at 5° C. for 1 h, at room temperature for 3 h and at 60° C. for 2 h. It is concentrated to dryness, the residue is taken up in EA, the EA solution is washed with 10% strength Na2SO3 solution and satd. NaCl solution, dried over MgSO4 and concentrated, and the residue is dried in a high vacuum. 38 g of the title compound result as a red oil.

Workup

  1. concentrationIt is concentrated to dryness
  2. washthe EA solution is washed with 10% strength Na2SO3 solution
  3. dry with materialNaCl solution, dried over MgSO4
  4. concentrationconcentrated
  5. customthe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-9bdf26f4873a41e1ad9b0cacf429ebdb
Source dataset
uspto-grants-1997_06
Patent number
US05635525

Reaction notes

Loading…