Buchwald–Hartwig amination: 1-Bromo-4-phenylmethoxybenzene → (R)-4-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)propyl)aniline

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

120 °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.

Copied from the source record, unedited

Palladium(II) acetate (0.427 g, 1.90 mmol) and dicyclohexyl(2',4',6'-triisopropylbiphenyl-2-yl)phosphine (0.906 g, 1.90 mmol) were added in one portion to a degassed solution of 1-(benzyloxy)-4-bromobenzene (5 g, 19.00 mmol), (R)-2-(tert- butyldimethylsilyloxy)propan-1-amine (4.32 g, 22.80 mmol) and Cesium carbonate (2.281 mL, 28.50 mmol) in toluene (75 mL) at 20°C under nitrogen. The resulting suspension was stirred at 120°C for 72 hours. The reaction mixture was diluted with EtOAc (150mL) and water (150mL) and the biphasic mixture was filtered through celite. The organic layer was seperated and washed sequentially with water (150mL) and saturated brine (150mL). The organic layer was evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution

This record comes from experimental reaction archive (ord-507c2159372a46eb8fb0f4b142612613). Open the source and check it against what is on this page.

• experimental reaction archive record ord-507c2159372a46eb8fb0f4b142612613 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.