HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → Methyl 4-bromo-5-methylfuran-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Methyl 4,5-Dibromo-2-furancarboxylate | HCID 4135083 | — |
| Reactant | HCID 178477798 | HCID 178477798 | — |
| Catalyst | Palladium Chloride | HCID 24290 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | Methyl 4-bromo-5-methylfuran-2-carboxylate | HCID 604544 | 1,830.4% |
Reaction Steps
To a mixture of the compound (1.80 g) obtained in Example 128a, palladium chloride(II) (0.02 g), triphenylphosphine (0.07 g) and tetrahydrofuran (30 mL) was added MeZnCl (2M tetrahydrofuran solution, 9.5 ml), and the mixture was heated under reflux for 4 hr under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, saturated aqueous ammonium chloride was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (carrier: silica gel, eluent: hexane ethyl acetate) to give the title compound (1.07 g) as a colorless solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08461348B2 |
| Source dataset | uspto-grants-2013_06 |
| ORD ID | ord-5f3bca02527d470a924e211a0b5035a5 |
| Source note | uspto-grants-2013_06 |