HuagongsheHuagongshe Chemistry Print Report · For research reference only
1,2-Dimethoxyethane → 2-Chloro-4-(4-methylphenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1,2-Dimethoxyethane | HCID 8071 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 2-Chloro-4-iodopyridine | HCID 1516511 | — |
| Reactant | (2'-Methyl-[1,1'-biphenyl]-4-yl)boronic acid | HCID 23005382 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Product | 2-Chloro-4-(4-methylphenyl)pyridine | HCID 44605216 | 44% |
Reaction Steps
A mixture of 2-chloro-4-iodopyridine (10.0 g, 41.8 mmol), p-tolylphenylboronic acid (5.68 g, 41.8 mmol), Pd(Ph3P)4 (1.45 g 1.25 mmol), sodium carbonate (13.3 g, 125 mmol), DME (300 mL) and water (75 mL) was degassed with nitrogen and then refluxed overnight. The reaction mixture was concentrated and extracted with ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and vacuum distilled and recrystallized to give 2-chloro-4-(p-tolyl)pyridine (3.75 g, 18.4 mmol, 44% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08946697B1 |
| Source dataset | uspto-grants-2015_02 |
| ORD ID | ord-58f2a078846c46cdb49b5a6dc4f3072b |
| Source note | uspto-grants-2015_02 |