Buchwald–Hartwig amination, record ord-c6d710180f5249588ab02dc546a2ae67
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 | Methyl 3,5-Dibromobenzoate | C₈H₆Br₂O₂ | |
| Reactant | Aniline | C₆H₇N | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 3-anilino-5-bromobenzoate | C₁₄H₁₂BrNO₂ | 0% |
Conditions
- Temperature
- 110 °C
Yield
- 0% of Methyl 3-anilino-5-bromobenzoate.
Procedure
Copied from the source record, unedited
aniline (0.380 g, 4.08 mmol), methyl 3,5-dibromobenzoate (1.000 g, 3.40 mmol), Pd(OAc)2 (0.076 g, 0.34 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.295 g, 0.51 mmol) and CESIUM CARBONATE (1.663 g, 5.10 mmol) were stirred in toluene (10 mL) and degassed with nitrogen for 15 minutes. The mixture was then heated at 110 °C under nitrogen for 24 hours. No evidence of any significant amount of product (ester or acid) therfore abandaned.
The source
This record comes from experimental reaction archive (ord-c6d710180f5249588ab02dc546a2ae67). Open the source and check it against what is on this page.
experimental reaction archive record ord-c6d710180f5249588ab02dc546a2ae67 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.