Buchwald–Hartwig amination: Bromobenzene → (3-(Phenylamino)phenyl)methanol
11% yield, run at 65 °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 | 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.
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
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.
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Where to next
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