[C-:1]#[N:2].[Na+].Br[CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15].C(Cl)Cl>CS(C)=O.CCOCC.O>[N:17]1([C:10]2[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:8]([CH:9]=2)[O:7][CH2:6][CH2:5][C:1]#[N:2])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1
Sodium cyanide (79 mg, 1.6 mmol) was added to 4-[3-(2-Bromo-ethoxy)-4-nitro-phenyl]-morpholine (447 mg, 1.35 mmol) in Dimethyl sulfoxide (5 mL) and the reaction was stirred at room temperature 48 h. The mixture was diluted with 50 mL Et2O and 20 mL water. DCM was added to solubilize ppt. The layers were separated and the aq. extracted 3×50 mL DCM. The combined organic extracts were washed with satd. sodium bicarbonate (50 mL) and brine (50 mL), conc. in vacuo and taken up in DCM for application to a 25 g SiO2 pre-load cartridge. Chromatography (0-100% EtOAc:Hex) afforded 3-(5-Morpholin-4-yl-2-nitro-phenoxy)-propionitrile as a yellow solid (212 mg, 57%). 1H-NMR (CDCl3): 8.01 (d, 1H, J=9.2 Hz), 6.52 (d, 1H, J=9.2 Hz), 6.40 (s, 1H), 4.31 (t, 2H, J=7.0 Hz), 3.86 (t, 4H, J=4.6 Hz), 3.35 (t, 4H, J=4.6 Hz), 2.93 (t, 2H, J=7.0 Hz).
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