HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → 2'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Carboxyphenylboronic Acid | HCID 312183 | — |
| Reactant | 2-(4-Bromo-3-methylphenyl)-5-methyl-1,3,4-oxadiazole | HCID 11436693 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 2'-Methyl-4'-(5-methyl-1,3,4-oxadiazol-2-yl)biphenyl-4-carboxylic acid | HCID 18690066 | 80.7% |
Reaction Steps
A stirred solution of 2-(4-bromo-3-methylphenyl)-5-methyl-1,3,4-oxadiazole (EP 0533268 A1) (0.21 g, 0.0008 mole) in a mixture of DME (10 ml) and water (30 ml) under argon was treated with 4-boronobenzoic acid (0.14 g, 0.0008 mole), sodium carbonate (0.39 g, 0.0037 mole) and tetrakis (triphenylphosphine)palladium (0) (16 mg), then heated under reflux for 4 hours. The mixture was acidified with 1M hydrochloric acid and extracted with ethyl acetate. The extract was dried (Na2SO4) and concentrated in vacuo to leave the title compound as a white solid (0.19 g, 78%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05972951 |
| Source dataset | uspto-grants-1999_10 |
| ORD ID | ord-620b843ed3f34df09829f391f87eadb4 |
| Source note | uspto-grants-1999_10 |