Buchwald–Hartwig amination, record ord-41642501237541609124229452d981cb
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 | 4-Bromo-2-fluorobenzaldehyde | C₇H₄BrFO | |
| Reactant | tert-Butyl carbamate | C₅H₁₁NO₂ | |
| Reagent | Cesium carbonate | CCs₂O₃ | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | (1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium | C₃₄H₂₈O₂Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | tert-butyl N-(3-fluoro-4-formylphenyl)carbamate | C₁₂H₁₄FNO₃ | 83.59% |
Conditions
- Temperature
- 100 °C
Yield
- 84% of tert-butyl N-(3-fluoro-4-formylphenyl)carbamate.
Procedure
Copied from the source record, unedited
A solution of 4-bromo-2-fluorobenzaldehyde (0.670 g, 3.30 mmol) dissolved in toluene (10 mL) was treated with tert-butyl carbamate (0.464 g, 3.96 mmol), rac-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.164 g, 0.26 mmol), Bis(dibenzylideneacetone)palladium (0.076 g, 0.13 mmol) and cesium carbonate (1.527 g, 4.69 mmol) under nitrogen. The mixture was degassed under vacuum several times before heating at 100 °C for 24 hours. Reaction incomplete so heated for further 10 hours. The reaction mixture was diluted with water (250 mL), and extracted with ethyl acetate (250 mL X 2). The organic was dried over magnesium sulfate, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 10% ethyl acetate in isohexane. Pure fractions were e
The source
This record comes from experimental reaction archive (ord-41642501237541609124229452d981cb). Open the source and check it against what is on this page.
experimental reaction archive record ord-41642501237541609124229452d981cb 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.