Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | 1-Naphthaleneboronic acid | HCID 254532 | — |
| Reactant | Potassium phosphate, tribasic, monohydrate | HCID 22031701 | — |
| Reactant | HCID 67151796 | HCID 67151796 | — |
| Catalyst | Tri-o-tolylphosphine | HCID 80271 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 58261495 | HCID 58261495 | 65% |
Reaction Steps
51 g (298 mmol) of 1-naphthylboronic acid, 100 g (298 mmol) of diethyl chlorobromoterephthalate and 144 g (626 mmol) of potassium phosphate monohydrate are initially introduced in a mixture of 600 ml of dist. water, 400 ml of toluene and 200 ml of dioxane and saturated with N2 for 30 min. 5.4 g (18 mmol) of tri(o-tolyl)phosphine and 669 mg (3 mmol) of palladium(II) acetate are subsequently added, and the mixture is heated at the boil for 3 h. After dilution with toluene, the organic phase is separated off, washed twice with water, dried over Na2SO4 and evaporated in vacuo. The oil which remains is distilled in a thin-film evaporator (p=5×10−3 mbar, T=130° C.) and isolated in the form of a yellow oil (74 g, 65%), which, according to 1H-NMR, has a purity of >95%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09051233B2 |
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| Source dataset | uspto-grants-2015_06 |
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| ORD ID | ord-11d263f48e514ee78b7d74e0cf9cc21c |
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| Source note | uspto-grants-2015_06 |
|---|