反应详情

温度

-78 °C

Lithium aluminum hydride (52.9 mL, 52.9 mmol) in THF (1.0M) was added to a solution of 2-(4-bromophenylamino)-2-(4-chlorophenyl)acetonitrile (20.0 g, 62.2 mmol) in THF (311 mL, 62.2 mmol) at −78° C. The reaction was allowed to stir at −78° C. and gradually warmed to room temperature over 4 hours. The reaction mixture was poured into 1N HCl. The solution was then basified and extracted with ethyl acetate (3×). The combined organic layers were washed with brine, dried and concentrated to give an oil. This residue was purified by column chromatography, eluting first with ethyl acetate/hexanes (2:1) then 5% MeOH/CH2Cl2→10% MeOH/CH2Cl2+1% NH4OH, affording N1-(4-bromophenyl)-1-(4-chlorophenyl)ethane-1,2-diamine as an oil (9.60 g, 49%). 1H NMR (400 MHz, CD3OD) δ □7.38 (d, 2H), 7.34 (d, 2H), 7.15 (d, 2H), 6.53 (d, 2H), 4.59 (dd, J=9.8, 4.7 Hz, 1H), 3.14 (dd, J=12.9, 4.7 Hz, 1H), 3.05 (dd, J=12.9, 9.4 Hz, 1H).

1. temperaturegradually warmed to room temperature over 4 hours
2. extractionextracted with ethyl acetate (3×)
3. washThe combined organic layers were washed with brine
4. customdried
5. concentrationconcentrated
6. customto give an oil
7. customThis residue was purified by column chromatography
8. washeluting first with ethyl acetate/hexanes (2:1)