HuagongsheHuagongshe Chemistry Print Report · For research reference only
Magnesium → 5-Cyclopropyl-1,3-benzodioxole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Magnesium | HCID 5462224 | — |
| Reactant | Benzene, 4-bromo-1-fluoro-2-phenoxy- | HCID 11076399 | — |
| Reactant | 1-(3-Acetoxy-2-fluoroprop-1-enyl)-1-(4-difluoromethoxyphenyl)cyclopropane | HCID 54437387 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 5-Cyclopropyl-1,3-benzodioxole | HCID 16205050 | 143.3% |
Reaction Steps
The method of Example 25 was repeated using a Grignard reagent, prepared from 4-fluoro-3-phenoxyphenyl bromide (0.31 g), tetrahydrofuran (2 ml) and magnesium (20 mg) and 1-(3-acetoxy-2-fluoroprop-1-enyl)-1-(4-difluoro-methoxyphenyl)cyclopropane (Example 24) (0.155 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 8 ml/min) to afford 1-(4-difluoromethoxyphenyl)-3-(4-fluoro-3-phenoxyphenyl)prop-1-enyl)-1-(3,4-methylenedioxyphenyl)cyclopropane (120 mg, 54%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05763700 |
| Source dataset | uspto-grants-1998_06 |
| ORD ID | ord-18d126dcb0e841bfa5ebfca8bff057e1 |
| Source note | uspto-grants-1998_06 |