HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → 4-(4-Nitrophenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Iodo-4-nitrobenzene | HCID 12495 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-(4-Nitrophenyl)pyridine | HCID 259219 | 42.1% |
Reaction Steps
To a mixture of 4-pyridylboronic acid (500 mg, 4.06 mmol), 1-iodo-4-nitrobenzene (1.01 g, 4.06 mmol) and Pd(Ph3P)2Cl2 (140 mg, 0.199 mmol) in dioxane (15 mL), a solution of Na2CO3 (1.00 g, 9.43 mmol) in H2O (10 mL) was added. The mixture was stirred at 100 C for 20 h. Water and EtOAc were added. Organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo. The residue was purified by a silica gel column on ISCO, eluted with 20-100% EtOAc in hexanes to give 4-(4-nitrophenyl)pyridine as a solid (342 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359308B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-d3768e4fd8a84ba98ff3cced20f9acf7 |
| Source note | uspto-grants-2016_06 |