Reaktion #728

Reaktionsgleichung

COc1cc(I)ccc1Br

NC1COC1

→

COc1cc(NC2COC2)ccc1B

Ausbeute 35.8%

Lösungsmittel

Cc1ccccc1

Reaktionsbedingungen

Vorschrift

A solution of 1-bromo-4-iodo-2-methoxybenzene (0.60 g, 1.92 mmol) dissolved in toluene (15 mL) was treated with oxetan-3-amine (0.140 g, 1.92 mmol), SODIUM TERT-BUTOXIDE (0.221 g, 2.30 mmol), XANTPHOS (0.111 g, 0.19 mmol) and TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (0.044 g, 0.05 mmol) under nitrogen. The resulting mixture was stirred at 80 °C in a sealed tube for 2 hours. The reaction mixture was diluted with water (10 mL), and extracted with ethyl acetate (3x 20 mL). The organic was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution 0-30% EtOAc in Heptane. Pure fractions were evaporated to dryness to afford N-(4-bromo-3-methoxyphenyl)oxetan-3-amine (0.177 g, 35.8 %) as a beige solid.

Quelle