HuagongsheHuagongshe Chemistry Print Report · For research reference only
Toluene → Methyl 3-(4-cyanobiphenylyl)acrylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 2-Propenoic acid, 3-(4-bromophenyl)-, methyl ester | HCID 816773 | — |
| Reactant | 4-Cyanophenylboronic acid | HCID 2734326 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | Methyl 3-(4-cyanobiphenylyl)acrylate | HCID 68583491 | — |
Reaction Steps
820 mg (3.4 mmol) of methyl 4-bromocinnamate were dissolved in 7 ml of dry toluene, added with 116 mg (0.1 mmol) of Pd(PPh3)4, a solution of 374 mg (1.1 mmol) of 4-cyanobenzeneboronic acid in 2 ml of MeOH, 6.8 ml of 2M Na2CO3 in water, and refluxed 9 h. Addition of EtOAc, washing with water, then with brine, filtration and flash chromatography (Merck silicagel) with Hexane/EtOAc mixtures 9/1 gave 273 mg of methyl 3-(4-cyanobiphenylyl)acrylate, mp. 150-152° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07728039B2 |
| Source dataset | uspto-grants-2010_06 |
| ORD ID | ord-6c1398decc134fd89f74b9803ea17d10 |
| Source note | uspto-grants-2010_06 |