Buchwald–Hartwig amination: 1-Bromo-2-chlorobenzene → N'-(2-chlorophenyl)ethane-1,2-diamine
0% yield, run at 140 °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-chlorobenzene | C₆H₄BrCl | |
| Reactant | Ethylenediamine | C₂H₈N₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Phosphine, tris(4-methylphenyl)- | C₂₁H₂₁P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | N'-(2-chlorophenyl)ethane-1,2-diamine | C₈H₁₁ClN₂ | 0% |
Conditions
- Temperature
- 140 °C
Yield
- 0% of N'-(2-chlorophenyl)ethane-1,2-diamine.
Other recorded runs with the same starting material
No other run in the library makes this product. These runs of the same class start from one of the same reactants, which is the nearest company this record has.
Procedure
Copied from the source record, unedited
Ref: R2239 To a mixture of 1-bromo-2-chlorobenzene (0.824 g, 4.30 mmol), tri-p- tolylphosphine (0.262 g, 0.86 mmol), sodium 2-methylpropan-2-olate (0.414 g, 4.30 mmol), diacetoxypalladium (0.097 g, 0.43 mmol) in toluene (4 mL) was added ethane-1,2-diamine (1.293 g, 21.52 mmol). The mixture was heated with microwave at 140 °C for 1 h. No product was formed.
The source
This record comes from experimental reaction archive (ord-5911a740f60145b0bc355f2a886b772f). Open the source and check it against what is on this page.
experimental reaction archive record ord-5911a740f60145b0bc355f2a886b772f 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
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