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  (Process Chem)


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Substitution (Br)



Example 1

A solution of the SM (80.0 g, 286 mmol) and TMSCN (28.2 g, 286 mmol) in ACN (600 mL) was stirred at RT for 30 min. The mixture was cooled to 0 C and treated with TBAF (74.6 g, 286 mmol). The reaction mixture was stirred for 12 h, after which time it was diluted with H2O and extracted with EtOAc. The org layer was separated, dried (Na2SO4), and concentrated. The residue was purified by silica gel flash chromatography to provide the product. [39 g, 60%]

[Patent Reference: WO2016014463, page 101, (6.7 MB)]