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

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Reaction Steps

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.

Provenance & Evidence