HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(2-(Trifluoromethoxy)phenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | 1-Bromo-2-(trifluoromethoxy)benzene | HCID 2777266 | — |
| Reactant | Dichloromethane methanol | HCID 21226129 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-(2-(Trifluoromethoxy)phenyl)pyridine | HCID 46317166 | 51% |
Reaction Steps
To a solution of (commercially available) (1-bromo-2-trifluoromethoxy-benzene) in DME (first degased with argon) under argon was added 3 mol % Pd(PPh3)4, pyridyl-4-boronic acid and 2N Na2CO3, the resulting reaction mixture was vigorously stirred under reflux. After 5 h at reflux, reaction as monitored by TLC showed completion. Two phases were separated, evaporation of most of the DME, redissolution of the residue in EtOAc and washing with aq. NaOH followed by evaporation gave a yellow oil. Flash Chromatography on SiO2 gel with a mixture of CH2Cl2/MeOH gave the title compound in 51% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07781436B2 |
| Source dataset | uspto-grants-2010_08 |
| ORD ID | ord-4781d7a064604a9088250c56dbbcb926 |
| Source note | uspto-grants-2010_08 |