HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triphenylphosphine → 5-Ethenyl-1,3-dihydro-2H-2-benzothiophene-2,2-dione
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Vinyltrimethylsilane | HCID 79102 | — |
| Reactant | 5-Bromo-1,3-dihydro-benzo(c)thiophene 2,2-dioxide | HCID 288396 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 5-Ethenyl-1,3-dihydro-2H-2-benzothiophene-2,2-dione | HCID 59801479 | — |
Reaction Steps
Under classical Heck reaction conditions, 5-Bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide was transformed with PPh3, Pd(OAc)2, TEA, and vinyltrimethylsilane at 90° C. in DMF. The crude product was extracted with CH2Cl2 and concentrated. Deprotection in CH2Cl2/TFA gave the pure product after purification with flash chromatography (CH2Cl2) in high yields.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08492510B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-5eaaf0e269454a8a85cd962bc79c425b |
| Source note | uspto-grants-2013_07 |