Buchwald–Hartwig amination: 1,4-Dibromobenzene → 1-(4-Bromophenyl)-3-methylazetidine

Drawn from the record's atom map: which bonds break and which form between the reactants and products the source listed. It shows a change in connectivity, not a simulated trajectory and not a mechanism.

Temperature

100 °C

Only the dimensions the source stated are listed. Anything absent here was not recorded, and it is not inferred from what the class usually needs.

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.

• Ethyl 1-(4-bromophenyl)piperidine-4-carboxylate59%
• Methyl 1-(4-bromophenyl)pyrrolidine-3-carboxylate32%
• Methyl 2-(4-(4-bromophenyl)piperazin-1-yl)acetate0%

Copied from the source record, unedited

3-methylazetidine (0.5 g, 4.69 mmol), diacetoxypalladium (10.53 mg, 0.05 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (0.058 g, 0.09 mmol) and cesium carbonate (3.67 g, 11.26 mmol), degassed toluene (15 mL) were heated at 100 °C over the weekend. The RM was filtered and washed with EtOAc the filtrate was then concentrated and the crude product purified by flash silica chromatography, elution gradient 20 to 30% EtOAc in heptane. Purest fractions were collected and combined with EN05604-93. The combined product was then recrystalised from EtOAc to give 1-(4-bromophenyl)-3-methylazetidine (0.899 g, 85 %).

This record comes from experimental reaction archive (ord-1e9ec853eb3e43adb71af85c977827e9). Open the source and check it against what is on this page.

• experimental reaction archive record ord-1e9ec853eb3e43adb71af85c977827e9 from dataset "750 AstraZeneca ELN dataset" (url: https://chemrxiv.org/engage/chemrxiv/article-details/60c9e3f37792a23bfdb2d471). No atom mapping is provided by the source.

  experimental record · quality medium · source

experimental reaction record.