反应详情

温度

60 °C

A mixture of 5-bromo-2-chloroaniline (2.0 g, 9.74 mmol), morpholine (4.3 mL, 49 mmol), 2-dicyclohexylphosphino-2,4,6,-triisopropylbiphenyl, (X-Phos) (0.37 g, 0.79 mmol), and tris(dibenzylideneacetone)dipalladium (0) (0.37 g, 0.4 mmol) in dry THF (20 mL) was degassed by nitrogen. To this mixture was added 1.0M lithium bis(trimethylsilyl)amide in THF (54 mL) dropwise, and the resulting reaction was heated to 60° C. After 2 h, the reaction was cooled to rt then cond under reduced pressure to ˜5 mL. After pouring into water, the mixture was extracted twice with EtOAc and twice with DCM. After the combined organic layers were dried over anhydrous magnesium sulfate, filtration, and concentration, the residue was purified on silica gel (0-30% EtOAc in hexanes) to yield 2-chloro-5-morpholinoaniline. 1H NMR (400 MHz, CDCl3) δ ppm 7.19 (1H, m), 6.41 (2H, m), 4.00 (2H, br. s.), 3.93 (4H, m), 3.22 (4H, m).

1. customwas degassed by nitrogen
2. additionTo this mixture was added 1.0M lithium bis(trimethylsilyl)amide in THF (54 mL) dropwise
3. customthe resulting reaction
4. temperaturethe reaction was cooled to rt
5. extractionthe mixture was extracted twice with EtOAc and twice with DCM
6. dry with materialAfter the combined organic layers were dried over anhydrous magnesium sulfate, filtration, and concentration
7. customthe residue was purified on silica gel (0-30% EtOAc in hexanes)