HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium vinyltrifluoroborate → 4-fluoro-5-vinyl-3H-isobenzofuran-1-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium vinyltrifluoroborate | HCID 23679353 | — |
| Reactant | 5-Bromo-4-fluoro-1,3-dihydro-2-benzofuran-1-one | HCID 66644038 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 4-fluoro-5-vinyl-3H-isobenzofuran-1-one | HCID 66644176 | — |
Reaction Steps
A mixture of 5-bromo-4-fluoro-2-benzofuran-1(3H)-one (5.0 g, 21.6 mmol), potassium vinyltrifluoroborate (4.4 g, 32.5 mmol) and Pd(dppf)Cl2 (500 mg) in 100 mL of TEA and 100 mL of EtOH was heated to reflux under N2 for 4 hrs and then concentrated. The resulting oil was purified by column chromatography to give 4-fluoro-5-vinyl-3H-isobenzofuran-1-one. 1H-NMR (400 MHz, CDCl3) δ ppm 7.67-7.68 (m, 2H), 6.90-6.97 (m, 1H), 6.00 (d, J=17.2 Hz, 1H), 5.60 (d, J=11.0 Hz, 1H), 5.35 (s, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08952166B2 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-fc27557475df4770a555e0f18a477a32 |
| Source note | uspto-grants-2015_02 |