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SNAr (Cl)

(Aliphatic Thiols)


Example 1

A suspension of NaH (60% dispersion on mineral oil, 413 mg, 10.32 mmol) in dry DMF (12 mL) at 0 C was treated dropwise with the thiol (B) (1.21 mL, 10.32 mmol). After the addition the mixture was stirred at RT for 15 min. The aryl chloride (A) (1.00 g, 3.44 mmol) was added and the reaction mixture was stirred at RT for 18 h, 80 C for 8 h, then allowed to cool overnight. The mixture was diluted with EtOAc, washed with H2O, brine, dried (Na2SO4), and concentrated in vacuo. The resulting material was purified by silica gel column chromatography (30-50% EtOAc/cyclohexane) to provide the product. [659 mg, 51%]

[Patent Reference: WO2015177325, page 71, (4.3 MB)]