4-Bromophenacyl bromide → Ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate

HRID 18639

Reaction equation

HRID 18639 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[C:12]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:13][C:14]([CH3:16])=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[C:14]([CH:13]([CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4])[C:12]([O:18][CH2:19][CH3:20])=[O:17])(=[O:15])[CH3:16]

Participants

5

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate

Product 1

HCID 14173974Ethyl 2-acetyl-4-(4-bromophenyl)-4-oxobutanoate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2,4′-dibromoacetophenone (3.0 g, 10.8 mmol), ethyl acetoacetate (1.48 mL, 10.8 mmol) and potassium carbonate (4.5 g, 32.4 mmol) were heated in 2-butanone (50 mL) at reflux for 24 hours. Upon cooling, the mixture was filtered over diatomaceous earth and concentrated. The residue was purified by chromatography with DCM to provide the title compound as an oil. 1H NMR (CDCl3) δ ppm 1.30 (3H), 2.10 (3H), 3.19 (2H), 3.75 (1H), 4.15 (2H), 7.50 (2H), 7.81 (2H); MS (ESI) m/z 326/328.

Workup

  1. temperatureat reflux for 24 hours
  2. temperatureUpon cooling
  3. filtrationthe mixture was filtered over diatomaceous earth
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography with DCM

Sources & evidence

ORD record
ord-bfcda754581f492fbdf500441de8d793
Source dataset
uspto-grants-2010_06
Patent number
US07741364B2

Linked notes

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