p-Bromoacetophenone → 1-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-1,3-dione

HRID 2090514Notes

Reaction equation

HRID 2090514 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([CH2:13][C:14]([O:16]C)=O)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH3:26])=[CH:21][CH:20]=1>CCOCC>[Br:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=[O:27])[CH2:26][C:14](=[O:16])[CH2:13][C:7]2[CH:8]=[CH:9][C:10]([O:11][CH3:12])=[C:5]([O:4][CH3:3])[CH:6]=2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 7466p-BromoacetophenoneHCID 24758Sodium hydrideHCID 85213Benzeneacetic acid, 3,4-dimethoxy-, methyl ester

Product 1

HCID 591887201-(4-Bromophenyl)-4-(3,4-dimethoxyphenyl)butane-1,3-dioneYield 50.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Sodium hydride (60% dispersion, 3.80 g, 95.1 mmol) was added portionwise to methyl 2-(3,4-dimethoxyphenyl)acetate (10 g, 47.6 mmol) in Et2O (100 ml) at 0° C. A solution of 4′-bromoacetophenone (9.48 g, 47.6 mmol) in Et2O (50 ml) was added dropwise over 1 h. The mixture was heated at reflux for 16 h, cooled, poured into ice/HCl (2 M), extracted with Et2O (3×100 ml), dried (MgSO4) and the solvent removed under reduced pressure. The residue was crystallized from MeOH to give the title compound (9 g, 50%) as a tan powder.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 16 h
  3. temperaturecooled
  4. extractionextracted with Et2O (3×100 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe residue was crystallized from MeOH

Sources & evidence

ORD record
ord-8a89e9ab370b4e7eb95f337133cf722e
Source dataset
uspto-grants-2013_05
Patent number
US08436184B2

Reaction notes

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