Buchwald–Hartwig amination: 1,4-Dibromobenzene → Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate
29% yield, run at 85 °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 | 1,4-Dibromobenzene | C₆H₄Br₂ | |
| Reactant | Methyl Pyrrolidine-3-carboxylate | C₆H₁₁NO₂ | |
| Reagent | sodium 2-methylpropan-2-olate | C₄H₉NaO | |
| Catalyst | Binap, (A+-)- | C₄₄H₃₂P₂ | |
| Catalyst | Bis(dibenzylideneacetone)palladium | C₅₁H₄₂O₃Pd₂ | |
| Solvent | Toluene | C₇H₈ | |
| Product | Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate | C₁₂H₁₄BrNO₂ | 29.15% |
Conditions
- Temperature
- 85 °C
Yield
- 29% of Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate.
Procedure
Copied from the source record, unedited
A suspension of methyl pyrrolidine-3-carboxylate (800 mg, 6.19 mmol), 1,4-dibromobenzene (1461 mg, 6.19 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (142 mg, 0.15 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (289 mg, 0.46 mmol) and Sodium Tert-Butoxide (714 mg, 7.43 mmol) in anhydrous toluene (30 mL) was stirred at 85 °C under nitrogen for 4 hours. The reaction was cooled to ambient temperature, diluted with Ether (100 mL) and filtered through celite. The filtrate was evaporated in vacuo to yield crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in heptane. Pure fractions were evaporated to dryness to afford methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate (513 mg, 29.1 %) as a yellow solid.
The source
This record comes from experimental reaction archive (ord-cb0ae83e039e422babb6d81e64a4df69). Open the source and check it against what is on this page.
experimental reaction archive record ord-cb0ae83e039e422babb6d81e64a4df69 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
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