Sodium Iodide → Tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane

Participants

Reaction Conditions

Reaction Steps

To a solution of 2,3-difluoro-4-methyl-5-nitro-phenol (1.02 g, 5.39 mmol) in NMP (10 ml) was added cesium carbonate (2.28 g, 7.01 mmol), sodium iodide (0.807 g, 5.39 mmol) and 2-bromoethoxy tertbutyldimethylsilane (1.5 ml, 7.01 mmol). The mixture was heated at 100° C. for one hour, then cooled to room temperature. Water was added and the mixture was extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 9:1) gave 1.16 g (62%) of tert-butyl-[2-(2,3-difluoro-4-methyl-5-nitro-phenoxy)-ethoxy]-dimethyl-silane as a tan solid.

Provenance & Evidence