HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,5-Dibromo-1,3,4-thiadiazole → HCID 22104437, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2,5-Dibromo-1,3,4-thiadiazole | HCID 3092530 | — |
| Reactant | 4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride) | HCID 3977284 | — |
| Catalyst | Ethanol | HCID 702 | — |
| Catalyst | Water | HCID 962 | — |
| Catalyst | Toluene | HCID 1140 | — |
| Catalyst | Sodium Carbonate | HCID 10340 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 22104437 | HCID 22104437 | 65% |
Reaction Steps
4-Octyloxyphenylboronic acid (5.9 g, 23.6 mmol) and 2,5-dibromo-1,3,4-thiadiazole (5.8 g, 23.6 mmol) are refluxed for 14 hours in a mixture of sodium carbonate (19.56 g), toluene (70 ml), ethanol (35 ml) and water (35 ml) and tetrakis(triphenylphosphine)palladium(0) (10 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2Cl2) give 5.6 g (65% of theory) of 2-bromo-5-(4-octyloxyphenyl)-1,3,4-thiadiazole.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05847149 |
| Source dataset | uspto-grants-1998_12 |
| ORD ID | ord-dcd20352d9824954aea9788e56b49db3 |
| Source note | uspto-grants-1998_12 |