Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Bromobenzyl cyanide | HCID 29625 | — |
| Reactant | 2-Methylphenyl boronic acid | HCID 2733267 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Water | HCID 962 | — |
| Product | HCID 86710276 | HCID 86710276 | 74.3% |
Reaction Steps
In a vial, 2-bromophenylacetonitrile (2 g, 10.2 mmol), 2-methylphenylboronic acid (1.53 g, 11.2 mmol) and potassium carbonate (2.82 g, 20.4 mmol, Eq: 2) were combined with toluene (15.0 ml), ethanol (15 ml) and water (5 ml) to give a light brown suspension. The mixture was degassed with argon and then tetrakis(triphenylphosphine)palladium(0) (354 mg, 306 μmol) was added. The reaction mixture was heated at 90° C. for 12 h, cooled and poured into water and extracted with EtOAc. The organic phase was washed with brine, dried (Na2SO4) and evaporated to dryness under reduced pressure. Chromatography (silica gel, 0% to 5% EtOAc in hexanes) provided the title product as a colourless oil (1.57 g; 74%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08921388B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-223a498ec86b4e1e9a941b45327dc42e |
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| Source note | uspto-grants-2014_12 |
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