[OH:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Cl:25][CH2:26][CH2:27][CH2:28]I>CC#N>[Cl:25][CH2:26][CH2:27][CH2:28][O:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5]([C:10]2([C:14]#[N:15])[CH2:11][CH2:12][CH2:13]2)=[C:4]([N+:16]([O-:18])=[O:17])[CH:3]=11-(4-(Hydroxyl)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile (0.5 g, 2 mmol) in MeCN (10 mL) was treated with potassium carbonate (0.306 g, 2.2 mmol) and 1-chloro-3-iodopropane (0.425 mL, 4 mmol) and stirred at 80° C. for 3 hours. The reaction mixture was concentrated, extracted with dichloromethane and washed with brine. The organic layer was dried (MgSO4), filtered and concentrated. Purification by flash chromatography (silica gel, 5-24% EtOAc/hexane) afforded 0.63 g (96%) of 1-(4-(3-chloropropoxy)-5-methoxy-2-nitrophenyl)cyclobutanecarbonitrile. MS (ESI) m/z 325 (M+H)+.
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