Phenacyl bromide → 1-(4-METHOXY-PHENYL)-4-PHENYL-BUTANE-1,4-DIONE

HRID 1725166Notes

Reaction equation

HRID 1725166 reaction equation
C(NCC)C.CC(O)(C)C.[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH3:20])=[CH:15][CH:14]=1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25]>C1(C)C=CC=CC=1.[Cl-].[Zn+2].[Cl-]>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:21])[CH2:20][CH2:23][C:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 6259Phenacyl bromideHCID 6386tert-ButanolHCID 74764'-MethoxyacetophenoneHCID 8021Diethylamine

Product 1

HCID 28172391-(4-METHOXY-PHENYL)-4-PHENYL-BUTANE-1,4-DIONEYield 36.7%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 1140TolueneSolvent

Procedure

To a vigorously stirred mixture of zinc chloride (5 g, 36.6 mmol) in anhydrous toluene (200 mL) is added a mixture of diethylamine (2.82 mL, 27.5 mmol) and t-BuOH (2.61 mL, 27.5 mmol) under Argon. After 1 h, 4′-methoxyacetophenone (4.12 g, 27.45 mmol) and 2-bromoacetophenone 1 (3.64 g, 18.3 mmol) are added sequentially. The mixture is stirred for 3 days at room temperature. The mixture is washed with 5% H2SO4 (200 mL) and the organics separated. The aqueous layer is washed with ethyl acetate (2×100 mL). The organics are combined, dried over sodium sulfate, filtered and concentrated in vacuo. Silica gel column chromatography (hexane/ethyl acetate (5→15%)) afforded 1-(4-Methoxy-phenyl)-4-phenyl-butane-1,4-dione (1.8 g), characterized by LCMS (Obs: 269.09, Cal: 268.11) and 1H NMR.

Workup

  1. additionis added
  2. washThe mixture is washed with 5% H2SO4 (200 mL)
  3. washThe aqueous layer is washed with ethyl acetate (2×100 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-435cf7ba41824bd7b99f538460c6d4c9
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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