Boron trifluoride etherate → 4-(1-Aminocyclopropyl)benzonitrile

Beteiligte Stoffe

Reaktionsschritte

Terephthalonitrile (500 mg, 390 mmol) was dissolved in 10 ml of DCM. Ti(OiPr)4 (1.1 ml, 3.9 mmol) was added to the solution, followed by a 3M solution of ethylmagnesium bromide in THF (2.3 ml, 7.0 mmol). The mixture was aged for 45 min at RT and BF3.Et2O (890 ul, 7.0 mmol) was added. The mixture was then aged for an additional 2 h at RT. The reaction was quenched with NH4Cl and 3N HCl. The layers were separated and the aqueous layer was washed with ether. The aqueous layer was then basicified using 10N NaOH (pH 9-10). EtOAc was added and the biphasic mixture was filtered. The layers were cut and the aqueous layer extracted with EtOAc. The combined organic layers were dried with MgSO4, filtered and concentrated. Yield=15%.

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