Buchwald–Hartwig amination, record ord-8e16338c39aa405d9e6607bfaa8d820e
One recorded run of this reaction. Below is what the source recorded, and nothing added to it.
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 4-Bromophenol | C₆H₅BrO | |
| Reactant | 1-Methylpiperazine | C₅H₁₂N₂ | |
| Reagent | lithium bis(trimethylsilyl)azanide | C₆H₁₈LiNSi₂ | |
| Catalyst | 2,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecane | C₁₈H₃₉N₄P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 4-(4-Methyl-1-piperazinyl)phenol | C₁₁H₁₆N₂O | 50.99% |
Conditions
- Temperature
- 80 °C
Yield
- 51% of 4-(4-Methyl-1-piperazinyl)phenol.
Procedure
Copied from the source record, unedited
diacetoxypalladium (0.039 g, 0.17 mmol) was added in one portion to 4-bromophenol (3 g, 17.34 mmol) and 1-methylpiperazine (2.308 mL, 20.81 mmol) in toluene (87 mL) at 25°C under nitrogen. To this was added toluene (87 mL) then a solution of 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.123 mL, 0.35 mmol) in Toluene (1 mL) and finally 1M LITHIUM BIS(TRIMETHYLSILYL)AMIDE (39.9 mL, 39.88 mmol) in THF was added dropwise over 1 minute. The resulting mixture was stirred at 80 °C for 18 hours. The reaction was allowed to cool to room temperature, SiO2 (23g) was added and evaporated to dryness. The crude product was purified by flash silica chromatography (120g), elution gradient 0 to 10% MeOH in EtOAc. Pure fractions were evaporated to dryness to afford 4-(4-methylpiperaz
The source
This record comes from experimental reaction archive (ord-8e16338c39aa405d9e6607bfaa8d820e). Open the source and check it against what is on this page.
experimental reaction archive record ord-8e16338c39aa405d9e6607bfaa8d820e 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
This is one experiment, not a rule. It says that on one occasion these species were combined under these conditions and this came out. It does not say the reaction will give the same result on your substrate, and nothing on the page has been generalised into a claim that it would.
The pathway is a separate question, kept on separate pages. A mechanism here is the canonical arrow pushing for a class, run on real structures and labelled rule-derived. It is not evidence, and this record is not a mechanism.