HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → Methyl 5-methyl-2-(pyridin-4-yl)benzoate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | Methyl 2-bromo-5-methylbenzoate | HCID 15110996 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Methyl 5-methyl-2-(pyridin-4-yl)benzoate | HCID 86680841 | 48.5% |
Reaction Steps
A mixture of methyl 2-bromo-5-methylbenzoate (5.2 g), pyridine-4-boronic acid (4.2 g), sodium carbonate (4.8 g), tetrakis(triphenylphosphine)palladium(0) (1.3 g), water (10 mL) and DME (50 mL) was heated under reflux overnight under a nitrogen atmosphere. The reaction mixture was diluted with ethyl acetate, and filtered through silica gel. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.5 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08648079B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-b876f2a939514c308aa6e1444869c4cd |
| Source note | uspto-grants-2014_02 |