HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 2,4-Dimethyl-6-(3-pyridinyl)phenol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Bromo-4,6-dimethylphenol | HCID 299976 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | 2,4-Dimethyl-6-(3-pyridinyl)phenol | HCID 90002455 | 70.3% |
Reaction Steps
2-bromo-4,6-dimethylphenol (1 g, 5 mmol) was dissolved in dimethoxyethane/water (2:1). Pyridin-3-ylboronic acid (0.62 g, 5 mmol) and Pd(dppf)Cl2 (0.20 g, 0.25 mmol), sodium carbonate (2.1 g, 25 mmol) were added thereto, followed by stirring for 1 hour under reflux. After the completion of the reaction, the reaction mixture was added with water, and extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate, concentrated under reduced pressure, and purified by column chromatography to obtain 2,4-dimethyl-6-(pyridin-3-yl)phenol (0.7 g, 70%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447083B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-d1d0cdab6b9e420f8018c3c663768b30 |
| Source note | uspto-grants-2016_09 |