Buchwald–Hartwig amination, record ord-45a7a9da12934ab5ab153542a819eb23
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 | Benzonitrile, 4-bromo- | C₇H₄BrN | |
| Reactant | Diethylamine | C₄H₁₁N | |
| Reagent | Potassium Carbonate | CK₂O₃ | |
| Catalyst | 2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl | C₃₃H₄₉P | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Acetonitrile | C₂H₃N | |
| Product | 4-(Diethylamino)benzonitrile | C₁₁H₁₄N₂ | 39.17% |
Conditions
- Temperature
- 160 °C
Yield
- 39% of 4-(Diethylamino)benzonitrile.
Procedure
Copied from the source record, unedited
4-Bromobenzonitrile (2.000 g, 10.99 mmol), diethylamine (3.41 mL, 32.96 mmol) and POTASSIUM CARBONATE (4.56 g, 32.96 mmol) were mixed in dry acetonitrile (10 mL) under argon in a microwave vial. The vial was sealed and heated with microvawes for 60 minutes at 160°C. Added diethylamine (3.41 mL, 32.96 mmol) and heated at 160°C for 3 hours. Added Palladium(II) acetate (0.123 g, 0.55 mmol) and 2-(Dicyclohexylphosphino)-2',4',6'-tri-i- propyl-1,1'-biphenyl (0.524 g, 1.10 mmol), purged with argon for 5 minutes and heated in an oil bath at 100°C for 24 hours. The reaction was cooled to rt and partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (40 mL). The layers were separated and the aqueous phase extracted with EtOAc (100 mL). The organics were combined, dried (Na2SO4), filtered
The source
This record comes from experimental reaction archive (ord-45a7a9da12934ab5ab153542a819eb23). Open the source and check it against what is on this page.
experimental reaction archive record ord-45a7a9da12934ab5ab153542a819eb23 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.