Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phosphate | HCID 1061 | — |
| Reactant | Methyl 2-bromobenzoate | HCID 11894 | — |
| Reactant | NAPHTHALENE-1,4-DIBORONIC ACID | HCID 10488882 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59776006 | HCID 59776006 | — |
Reaction Steps
1.55 g (0.1 mmol) of Pd(PPh3)4 are added to a vigorously stirred, degassed suspension of 21.6 g (7.1 mmol) of methyl 2-bromobenzoate, 10.1 g (28 mmol) of 1,4-naphthalenediboronic acid and 18.9 g (6.6 mmol) of trispotassium phosphate in a mixture of 350 ml of water and 350 ml of THF, and the mixture is refluxed for 60 h. After cooling, the organic phase is separated off, washed three times with 200 ml of water and once with 200 ml of saturated sodium chloride solution and subsequently dried over magnesium sulfate. The organic phase is evaporated to dryness under reduced pressure in a rotary evaporator. The grey residue obtained in this way is recrystallised from dioxane. The deposited crystals are filtered off with suction, washed with 50 ml of ethanol and subsequently dried under reduced pressure. Yield: 13 g, 82% of theory.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08748010B2 |
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| Source dataset | uspto-grants-2014_06 |
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| ORD ID | ord-d6fc4921cd544226ac7b590a57202f6b |
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| Source note | uspto-grants-2014_06 |
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