HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Dichloromethane → 5-Bromo-2-(3-methoxyphenyl)pyridine
Beteiligte Stoffe
| Rolle | Name | HCID | Einwaage |
|---|---|---|---|
| Edukt | Dichloromethane | HCID 6344 | — |
| Edukt | Cesium carbonate | HCID 10796 | — |
| Edukt | 2,5-Dibromopyridine | HCID 69353 | — |
| Edukt | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| Lösungsmittel | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Produkt | 2-Bromo-5-(3-methoxyphenyl)pyridine | HCID 15326155 | — |
| Produkt | 5-Bromo-2-(3-methoxyphenyl)pyridine | HCID 49758519 | 43% |
Reaktionsschritte
In a schlenck tube, a mixture of 2,5-dibromopyridine (2.11 mmol, 0.500 g), 3-methoxyphenylboronic acid (2.11 mmol, 0.321 g), PdCl2dppf.DCM (0.21 mmol, 0.172 g), Cs2CO3 (6.33 mmol, 2.063 g) in a dioxane/water 4:1 mixture (14.5 ml) was heated at 100° C. for 14 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The solid residue was purified by chromatography over SiO2 eluting with hexane/ethyl acetate mixtures affording 5-bromo-2-(3-methoxyphenyl)pyridine (0.242 g, yield 43%) as major product and 2-bromo-5-(3-methoxyphenyl)pyridine (0.039 g) as minor product.
Herkunft & Nachweise
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patentnummer | US08536165B2 |
| Quelldatensatz | uspto-grants-2013_09 |
| ORD ID | ord-3d31eae132414104885a110c6a7d5294 |
| Quellennotiz | uspto-grants-2013_09 |