Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sulfuric Acid | HCID 1118 | — |
| Reactant | Phenacyl bromide | HCID 6259 | — |
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Diethylamine | HCID 8021 | — |
| Reactant | 4'-Fluoroacetophenone | HCID 9828 | — |
| Catalyst | Zincchloride | HCID 3007855 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 57423673 | HCID 57423673 | 54.8% |
Reaction Steps
Diethylamine (55 mmol, 5.69 mL) and t-Butanol (55 mmol, 5.26 mL) are added to a stirred solution of Zinc Chloride (74 mmol, 10 g) in anhydrous toluene (100 mL). After two hours of stirring at room temperature, Zinc Chloride is completely dissolved. 1-(4-Fluorophenyl)-ethanone (40 mmol, 4.90 mL) is added, followed by the addition of bromoacetophenone (37 mmol, 7.4 g). The reaction is allowed to stir at room temperature for 3 days. A 5% aqueous solution of sulfuric acid (75 mL) is added and the organic phase is separated from the aqueous phase. The aqueous phase is extracted with Ethyl Acetate (50 mL) and the two organic phases are combined. The organic phase is dried with Sodium Sulfate, filtered and concentrated to give 1-(4-fluoro-phenyl)-4-phenyl-butane-1,4-dione (5.2 g) confirmed by LCMS, as a white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07488832B2 |
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| Source dataset | uspto-grants-2009_02 |
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| ORD ID | ord-8548ae5614ad461b9491f897205e9e63 |
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| Source note | uspto-grants-2009_02 |
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