Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 3-Tolylboronic acid | HCID 2733950 | — |
| Reactant | 2-Chloro-6-fluoroquinoline | HCID 15059433 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 59288845 | HCID 59288845 | 80.1% |
Reaction Steps
3-methylphenyl boronic acid (13 mmol), 2-chloro-6-fluoroquinoline (10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 mmol) and potassium carbonate (15 g) are put in a two-neck round-bottom flask and dissolved in tetrahydrofuran (THF) (30 mL) and H2O (10 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, THF and toluene are removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering, 2-(3-methylphenyl)-6-fluoroquinoline (1.9 g) is yielded.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08999476B2 |
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| Source dataset | uspto-grants-2015_04 |
|---|
| ORD ID | ord-5b12f72d9b2441b2bca2f9e512c732a8 |
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| Source note | uspto-grants-2015_04 |
|---|