Buchwald–Hartwig amination: 1-Bromo-4-iodobenzene → 2-(4-Bromophenyl)-1,3-dihydroisoindole
48% yield, run at 100 °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 | 1-Bromo-4-iodobenzene | C₆H₄BrI | |
| Reactant | Isoindoline | C₈H₉N | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | C₃₉H₃₂OP₂ | |
| Catalyst | Palladium (II) acetate | C₄H₈O₄Pd | |
| Solvent | Toluene | C₇H₈ | |
| Product | 2-(4-Bromophenyl)-1,3-dihydroisoindole | C₁₄H₁₂BrN | 48.3% |
Conditions
- Temperature
- 100 °C
Yield
- 48% of 2-(4-Bromophenyl)-1,3-dihydroisoindole.
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
palladium(II) acetate (0.112 g, 0.50 mmol) and XANTPHOS (0.288 g, 0.50 mmol) were added to a degassed solution of isoindoline (0.566 ml, 4.98 mmol), 1-bromo-4-iodobenzene (1.41 g, 4.98 mmol) and SODIUM TERT-BUTOXIDE (1.197 g, 12.46 mmol) in toluene (49.3 ml) under nitrogen. The resulting solution was stirred at 100 °C for 18 hours. The reaction mixture was allowed to cool to RT and was partitioned between EtOAc and H2O, filtered and the organic layer separated and dried over MgSO4, filtered and evaporated to dryness to give crude product. The crude product preabsorbed onto SiO2 and was purified by flash silica (40g, grace) chromatography, elution gradient 0 to 10% DCM in heptane. Pure fractions were evaporated to dryness to afford 2-(4-bromophenyl)isoindoline (0.660 g, 48.3 %) as an orange
The source
This record comes from experimental reaction archive (ord-be64b42a88614cc79bed55017a7f5289). Open the source and check it against what is on this page.
experimental reaction archive record ord-be64b42a88614cc79bed55017a7f5289 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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