Buchwald–Hartwig amination: 1-Bromo-2-chloro-4-fluorobenzene → 1-(2-Chloro-4-fluorophenyl)piperidin-4-one
0% yield, run at 120 °C, as recorded by experimental reaction archive. The written procedure is below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 1-Bromo-2-chloro-4-fluorobenzene | C₆H₃BrClF | |
| Reactant | 4-Piperidone | C₅H₉NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 1-(2-Chloro-4-fluorophenyl)piperidin-4-one | C₁₁H₁₁ClFNO | 0% |
Conditions
- Temperature
- 120 °C
Yield
- 0% of 1-(2-Chloro-4-fluorophenyl)piperidin-4-one.
Procedure
Copied from the source record, unedited
To a round bottom flask was added palladium(II) acetate (0.012 g, 0.06 mmol), dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.026 g, 0.06 mmol), and sodium tert-butoxide (0.213 g, 2.21 mmol). Added 5 mL toluene/t-butanol mix and purged with nitrogen. Added piperidin-4-one (0.15 g, 1.11 mmol), in 3 mL tol/tbuoh (slurry), followed by 1-bromo-2-chloro-4-fluorobenzene (0.255 g, 1.22 mmol), in 2 mL tol/tbuoh. Flushed with additional nitrogen and then heated to 120oC overnight. Let reaction mixture cool to room temperature and filtered through Celite. Rinsed repeatedly with EtOAc and concentrated in vacuo. Purified via ISCO 12g SiO2 column using 0-20% hexanes/ethyl acetate. Fractions 19 and 20 were combined and concentrated to afford a white solid. NMR (I200805922.42) shows a mess
The source
This record comes from experimental reaction archive (ord-5c5d7fac90d14102bcad7fe6bdad56a8). Open the source and check it against what is on this page.
experimental reaction archive record ord-5c5d7fac90d14102bcad7fe6bdad56a8 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.
How to read this record
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