1,4-Dioxane → HCID 86727067, compound

Participants

Reaction Conditions

Reaction Steps

To a 500 mL flask was added 5-bromo-4-fluoro-2-methoxybenzonitrile (4.00 g, 17.4 mmol), Bis(Triphenylphosphine)Palladium(II)Chloride (0.61 g, 0.87 mmol), tributyl(1-ethoxy-vinyl)tin (9.42 mL, 26.1 mmol) followed by addition of 1,4 dioxane (40 mL). The resulting mixture was stirred at 95° C. for 3 h; the flask was taken out of the oil bath and cooled to rt followed by treatment with a mixture of THF/H2O (50/25 mL) and placed in an ice bath. To the flask was added NBS (6.19 g, 34.8 mmol) in small portions; after stirred for 0.5 h at 0° C., LC indicated formation of the desired product. The reaction mixture was taken out of the ice bath and slowly warmed up to rt. The reaction mixture was extracted with EtOAc (3×100 mL), washed with brine and water, it was then dried (Na2SO4), filtered and concentrated to dryness followed by separation over silica gel with the solvent systems of hexanes/EtOAc (1/0.5) to give the desired product. LC/MS: [(M+2)]+=274.

Provenance & Evidence