Buchwald–Hartwig amination: Methyl 3,5-Dibromobenzoate → Methyl 3-anilino-5-bromobenzoate
0% yield, run at 110 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
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.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Reactants | Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|---|
| Methyl 3-bromo-5-iodobenzoate; Aniline | Binap, (A+-)-; Palladium (II) acetate | Cesium carbonate | Toluene | 110 °C | — | 41% |
| Methyl 3,5-Dibromobenzoate; Aniline | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine); Palladium (II) acetate | Cesium carbonate | Toluene | 110 °C | — | 0% (this run) |
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.
Where to next
More Buchwald–Hartwig amination records
Other runs of this class, one page per distinct transformation.
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