Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 4-Chloroanisole | HCID 12167 | — |
| Reactant | Pentapotassium Triphosphate | HCID 61695 | — |
| Reactant | Phenyl dihydrogen orthoborate | HCID 78412 | — |
| Reactant | Di-1-adamantylphosphine | HCID 11077518 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 4-Methoxybiphenyl | HCID 11943 | 84% |
Reaction Steps
Phenylboric acid (366 mg, 3.0 mmols), palladium acetate (4.49 mg, 0.02 mmols), diadamantyl phosphine (12.1 mg, 0.04 mmols) and potassium triphosphate (1.273 g, 6 mmols) are placed in 6 ml of dioxane and water (0.18 ml, 10 mmols) under argon. The reaction mixture is heated in an oil bath of 100° C. and stirred for 5 minutes. Afterwards, 4-chloroanisole (0.27 ml, 2 mmols) is added. The reaction mixture is then stirred for 18 hours at 100° C. and subsequently cooled. The title compound is purified by flash chromatography over silica gel. The yield is 84%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06548684B2 |
|---|
| Source dataset | uspto-grants-2003_04 |
|---|
| ORD ID | ord-58a126662e4643b78eb314c34ea9ba4d |
|---|
| Source note | uspto-grants-2003_04 |
|---|
