Tetrahydrofuran → 1-[4-Fluoro-2-(2-fluoro-phenylamino)-phenyl]-propan-1-one

Participants

Reaction Conditions

Reaction Steps

In a 500 mL round bottom flask, 4-fluoro-2-(2-fluoro-phenylamino)-N-methoxy-N-methyl-benzamide (6.0 g, 20.5 mmol) was added to THF (60 mL) to give a colorless solution. The reaction was cooled to 0° C. in an ice bath and ethyl magnesium bromide (3.0 M in THF, 27.4 mL, 82.2 mmol) was added slowly over a 15 min. period. The mixture was stirred at 0° C. for 4 hr. The reaction mixture was poured into ethyl acetate (250 mL) and washed with 1N HCl (1×150 mL), water (2×150 mL) and brine (2×150 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuum. The crude material was purified by flash chromatography using 20% ethyl acetate-hexanes to give 1-[4-fluoro-2-(2-fluoro-phenylamino)-phenyl]-propan-1-one (3.0 g, 56%).

Provenance & Evidence