HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethanol → 5-Bromo-3-chloro-2-(4-octyloxyphenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethanol | HCID 702 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-n-Octyloxyphenylboronic Acid (contains varying amounts of Anhydride) | HCID 3977284 | — |
| Reactant | 2,5-Dibromo-3-chloropyridine | HCID 12630983 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 5-Bromo-3-chloro-2-(4-octyloxyphenyl)pyridine | HCID 19050004 | 67.6% |
Reaction Steps
10.0 g (37.0 mmol) of 3-chloro-2,5-dibromopyridine, 11.11 g (44.4 mmol) of 4-octyloxybenzeneboronic acid, 7.85 g (74.0 mmol) of sodium carbonate and 0.46 g (0.4 mmol) of tetrakis(triphenylphosphine)palladium(0) are heated at 80° C. for 18 hours in 125 ml of toluene, 60 ml of ethanol and 60 ml of water. The mixture is subsequently partitioned between aqueous sodium chloride solution and ether, the organic phase is washed with aqueous sodium chloride solution, dried over sodium sulfate and evaporated, and the product is purified by chromatography (silica gel, dichloromethane:hexane =4:1), giving 9.93 g of 5-bromo-3-chloro-2-(4-octyloxyphenyl)pyridine. ##STR16##
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05629428 |
| Source dataset | uspto-grants-1997_05 |
| ORD ID | ord-264f0a4d3ec24122b522c7f18f5bc15e |
| Source note | uspto-grants-1997_05 |