Dichloromethane → 1-(3-(tert-Butyldimethylsilyloxy)-2,5-difluorophenyl)propan-1-one

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Reaction Steps

A 200 mL round bottom flask was charged with 90.C (0.48 g, 1.6 mmol), DCM (15 mL), iodobenzene diacetate (0.56 g, 1.7 mmol), and TEMPO (0.012 g, 0.079 mmol). The mixture was stirred overnight at room temperature and diluted with EtOAc. The organics were washed with saturated aqueous sodium thiosulfate, saturated aqueous sodium bicarbonate, and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (0-5% EtOAc/hexane) to afford 90.D (0.45 g, 94% yield) as a colorless oil.

Provenance & Evidence