Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 2,6-Dimethylphenylboronic acid | HCID 583322 | — |
| Reactant | Tri-tert-butylphosphine tetrafluoroborate | HCID 2734635 | — |
| Reactant | Methyl 3-Bromo-2-methylbenzoate | HCID 12929135 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 57413377 | HCID 57413377 | — |
Reaction Steps
To a two-neck round bottom flask with a magnetic stirring bar, was added tris(dibenzylideneacetone)dipalladium(0) (120 mg, 0.131 mmol), tri-t-butylphosphonium tetrafluoroborate (76 mg, 0.262 mmol), cesium fluoride (2.65 g, 17.5 mmol), 2,6-dimethylphenylboronic acid (1.3 g, 8.73 mmol), and the compound from Step A (1 g, 4.4 mmol). One neck of the flask was connected to a vacuum line while another neck was fitted with a argon balloon. The flask was then purged 8-10 times with argon. The vacuum line was replaced with a septum and anhydrous THF (10 mL) was added by syringe. The mixture was stirred in a 70° C. oil bath for 16 h. The reaction solution was filtrated and concentrated. The residue was purified by column chromatography on silica gel Biotage 40S™, eluting with EtOAc/hexane (10:1) to give the title compound as a clear oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399507B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-62c557948f0b405e960c343e8127cce4 |
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| Source note | uspto-grants-2013_03 |
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