Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | 6-Bromo-2-naphthalenol | HCID 27144 | — |
| Reactant | Potassium Phosphate, Tribasic | HCID 62657 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 1-Naphthaleneboronic acid | HCID 254532 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 59147628 | HCID 59147628 | — |
Reaction Steps
913 mg (3 mmol) of tri-o-tolylphosphine and then 112 mg (0.5 mmol) of palladium(II) acetate are added to a suspension of 111.5 g (500 mmol) of 6-bromo-2-naphthol, 111.8 g (650 mmol) of naphthaleneboronic acid and 224.1 g (1150 mmol) of tripotassium phosphate in a mixture of 1000 ml of toluene, 200 ml of dioxane and 1000 ml of water, and the mixture is heated under reflux for 18 h. After cooling, 200 ml of 2 N hydrochloric acid are added, and the organic phase is separated off, washed three times with 500 ml of 1 N hydrochloric acid, once with 500 ml of saturated sodium chloride solution, filtered through silica gel and evaporated to dryness in vacuo. The residue is recrystallised from 150 ml of toluene. Yield: 113.3 g (419 mmol), 83.8% of theory; purity: 98% according to NMR.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08114531B2 |
|---|
| Source dataset | uspto-grants-2012_02 |
|---|
| ORD ID | ord-5e4d00f6941f40e988a79b29004c49f1 |
|---|
| Source note | uspto-grants-2012_02 |
|---|