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  (Organic Chemistry)

SNAr (Cl)



Example 1

To a stirred solution of the SM (1.6 g, 3.55 mmol) in DMSO (30 mL) was added DABCO (80 mg, 0.71 mmol) and NaCN (209 mg, 4.26 mmol). H2O (10 mL) was added dropwise and the reaction mixture was stirred at 50 C for 16 h. After consumption of the SM by TLC, the reaction mixture was diluted with H2O (100 mL) and extracted with EtOAc (3 x 50 mL). The combined organics were dried (Na2SO4) and concentrated. The resulting material was purified by chromatography (2:1 PE/EtOAc) to provide the product as a white solid. [1.2 g, 77%]

[Patent Reference: WO2016011390, page 330, (20.2 MB)]