Buchwald–Hartwig amination: 2-Bromo-4-iodoanisole → 3-Bromo-4-methoxy-N-[(oxan-4-yl)methyl]aniline
10% yield, run at 80 °C, as recorded by experimental reaction archive. The written procedure is below. One of 2 recorded runs making this product; all of them are compared below.
The atoms, from reactants to products
What was in the flask
| Role | Species | Formula | Yield |
|---|---|---|---|
| Reactant | 2-Bromo-4-iodoanisole | C₇H₆BrIO | |
| Reactant | 4-Aminomethyltetrahydropyran | C₆H₁₃NO | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 3-Bromo-4-methoxy-N-[(oxan-4-yl)methyl]aniline | C₁₃H₁₈BrNO₂ | 10.42% |
Conditions
- Temperature
- 80 °C
Yield
- 10% of 3-Bromo-4-methoxy-N-[(oxan-4-yl)methyl]aniline.
Every recorded run making this product
2 runs of this class made the same product and differed in what else was in the flask. They are listed from the highest yield down, with this page's run marked.
| Catalyst | Reagents | Solvent | Temp. | Time | Yield |
|---|---|---|---|---|---|
| Binap, (A+-)-; Palladium (II) acetate | sodium 2-methylpropan-2-olate | Toluene | 80 °C | — | 10% (this run) |
| Binap, (A+-)-; Palladium (II) acetate | sodium 2-methylpropan-2-olate | 1,4-Dioxane | 80 °C | — | 0% |
Procedure
Copied from the source record, unedited
Palladium (II) acetate (0.032 g, 0.14 mmol) and racemic-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl (0.179 g, 0.29 mmol) were suspended in toluene (3 mL). The mixture was evacuated and purged with nitrogen, and warmed to 50°C. In a separate vessel, 2-bromo-4-iodo-1-methoxybenzene (0.6 g, 1.92 mmol), (tetrahydro-2H-pyran-4-yl)methanamine (0.221 g, 1.92 mmol) and sodium-t- butoxide (0.276 g, 2.88 mmol) were suspended in toluene (3.5 mL). The resulting mixture was evacuated, purged with nitrogen and warmed to 50°C. After ~30 mins, the catalyst mixture was transferred to the reaction vessel. The reaction was evacuated and purged with nitrogen and heated at 80°C overnight. The mixture was filtered and purified by flash silica chromatography, elution 30% EtOAc in heptane. Pure fractions were ev
The source
This record comes from experimental reaction archive (ord-bbf1fab9fbf9435cba74991837eb9bf4). Open the source and check it against what is on this page.
experimental reaction archive record ord-bbf1fab9fbf9435cba74991837eb9bf4 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
More Buchwald–Hartwig amination records
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