HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 1-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (4-Fluoro-3-phenoxyphenyl)methanesulfonyl fluoride | HCID 12113197 | — |
| Reactant | 2-Fluoro-3-cyclopropyl-3-(p-chlorophenyl)acrylaldehyde | HCID 54011500 | — |
| Catalyst | 18-Crown-6 | HCID 28557 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | 1-(p-Chlorophenyl)-1-cyclopropyl-2-fluoro-4-(4-fluoro-3-phenoxyphenyl)-1,3-butadiene | HCID 54035311 | 93% |
Reaction Steps
A mixture of p-chloro-β-cyclopropyl-α-fluoro-cinnamaldehyde (224.6 mg, 1 mmol), (4-fluoro-3-phenoxyphenyl)methanesulfonyl fluoride (312.7 mg, 1.1 mmol), potassium carbonate (552.8 mg, 4 mmol), and 18-crown-6 (13.2 mg, 0.05 mmol) in acetonitrile is stirred at room temperature overnight, quenched with water, and extracted with ethyl acetate. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product (380 mg, 94% pure by GC analysis, 93% yield) which is identified by 1H and 19F NMR spectral analyses.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06646166B1 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-2ef5e20f99904fe7b863639e5de3628e |
| Source note | uspto-grants-2003_11 |