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Activated Cl Formation

(POCl3 + Solvent + Base)


Example 1

To a flask containing the SM (5.0 g, 18.6 mmol) and DCE (93 mL) was added POCl3 (5.21 mL, 55.9 mmol), followed by DIEA (16.3 mL, 93 mmol). The flask was fitted with a reflux condenser and the mixture was stirred at 90 C for 2 h. The reaction mixture was diluted with H2O and the layers were separated. The aq layer was extracted with EtOAc. The combined organics were washed with brine, dried (Na2SO4), and concentrated. The resulting material was purified by column chromatography (0-75% EtOAc/heptane) to provide the product as a light yellow solid. [ 4.08 g, 76%] [WO2014201173, page 128]