Morpholine → 4-(3,5-Dichlorophenyl)morpholine

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To a solution of 3,5-dichloroiodobenzene (272 mg, 1 mmol) in anhydrous THF (3 mL) was added morpholine (200 μL, 2 mmol), catalytic (+/−) BINAP (6 mol %), catalytic Pd2(dba)3 (3 mol %) and sodium tert-butoxide (192 mg, 2 mmol). The mixture was sparged with N2 for 5 minutes, then the vial was sealed and heated at 80° C. for 18 h. The reaction mixture was directly purified via flash chromatography on silica gel, eluting with a 0-50% gradient of ethyl acetate/heptane to obtain 4-(3,5-dichlorophenyl)-morpholine as a white solid. 1H NMR (CDCl3, 400 MHz) δ 6.84 (t, J=1.71 Hz, 1H), 6.75 (d, J=1.77 Hz, 2H), 3.81-3.87 (m, 4H), 3.13-3.19 (m, 4H). MS (m/z) 232.2 (M+1).

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