HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylboronic Acid → 2-Bromo-5-phenyl-1,3,4-thiadiazole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | 2,5-Dibromo-1,3,4-thiadiazole | HCID 3092530 | — |
| Catalyst | Ethanol | HCID 702 | — |
| Catalyst | Water | HCID 962 | — |
| Catalyst | Toluene | HCID 1140 | — |
| Catalyst | Sodium Carbonate | HCID 10340 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dichloromethane ethylacetate | HCID 21226138 | — |
| Product | 2-Bromo-5-phenyl-1,3,4-thiadiazole | HCID 13104117 | 38% |
Reaction Steps
Phenylboronic acid (2.0 g, 16.4 mmol) and 2,5-dibromo-1,3,4-thiadiazole (4.0 g, 16.4 mmol) are refluxed for 24 hours in a mixture of sodium carbonate (15.64 g), toluene (60 ml), ethanol (30 ml) and water (30 ml) and tetrakis(triphenylphosphine)palladium(0) (10 mol %) as catalyst. Aqueous work-up and column chromatography (SiO2, CH2Cl2 /ethyl acetate 9:1) give 1.5 g (38% of theory) of 2-bromo-5-phenyl-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-87e6dd7e1b7044e49f352cc311bd2e79 |
| Source note | uspto-grants-1998_12 |