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

HRID 1913383

Reaction equation

HRID 1913383 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-da8198338e8a49c3a9c43e255fc3967e
Source dataset
uspto-grants-2013_12
Patent number
US08609713B2

Linked notes

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