Chlorotrimethylsilane → HCID 67252001, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of zinc powder (0.98 g, 15.0 mmol) in anhydrous THF (30 mL) was added TMSCl (0.39 mL, 3.0 mmol) at 40° C. The resulting mixture was stirred at 55° C. for 15 min and then cooled to 37° C. Ethyl 2-bromoacetate (1.35 mL, 12.0 mmol) was added at 37° C. and the reaction mixture was stirred at this temperature for 30 min. To a solution of 2-fluoro-4-(tetrahydro-2H-pyran-2-yloxy)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (1.05 g, 3.0 mmol) in anhydrous THF (40 mL) was added dropwise above prepared solution at −78° C. The reaction was allowed to stir at room temperature for 1.5 h and quenched by addition of aqueous ammonium chloride (20 mL). The resulting mixture was extracted with ethyl acetate (2×50 mL) and the combined organic layers were dried over anhydrous Na2SO4, concentrated in vacuo. The residue was purified by column chromatography (EtOAc/PE=1/3) on silica gel to give the title compound as a yellow solid. (0.89 g, Yield: 87.9%). MS (ESI) m/z=339 [M+H]+.

Provenance & Evidence