Buchwald–Hartwig amination, record ord-b4111a9cc1ab4be8bf9e586d821e9697
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 | Bromobenzene | C₆H₅Br | |
| Reactant | 3-Aminobenzyl alcohol | C₇H₉NO | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Tetrahydrofuran | C₄H₈O | |
| Product | (3-(Phenylamino)phenyl)methanol | C₁₃H₁₃NO | 11.13% |
Conditions
- Temperature
- 65 °C
Yield
- 11% of (3-(Phenylamino)phenyl)methanol.
Procedure
Copied from the source record, unedited
A solution of Tris(dibenzylideneacetone)dipalladium(0) (0.178 g, 0.19 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (0.282 g, 0.49 mmol) in THF (20 mL) (degassed) was heated to 50 ºC under a nitrogen atmosphere for 30 min. (3-(phenylamino)phenyl)methanol (0.072 g, 11.13 %) (0.4 g, 3.25 mmol) and cesium carbonate (2.117 g, 6.50 mmol) were added followed by bromobenzene (0.409 mL, 3.90 mmol) and the mixture stirred at 65 °C over two days. The reaction mixture was cooled to room temperature then diluted with DCM and filtered. stirred with SiliCycle SiliMet-SH (1 g) for 3 h at 60 °C. The mixture was filtered through an acrodisc glassfiber filter, 25 mm, 1.0 µm. The filtrate (clear) was concentrated to give crude product (1,00 g). The crude was dissolved in DMSO and the p
The source
This record comes from experimental reaction archive (ord-b4111a9cc1ab4be8bf9e586d821e9697). Open the source and check it against what is on this page.
experimental reaction archive record ord-b4111a9cc1ab4be8bf9e586d821e9697 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.