Diethyl Ether → HCID 71208293, compound

Participants

Reaction Steps

To a solution of 4-fluoro-N-methoxy-N-methyl-2-phenylamino-benzamide (9.35 g, 34.1 mmol) in THF (170 mL) was added ethylmagnesium bromide (1M solution in THF) (136 mL, 136 mmol) dropwise at 0° C. under nitrogen. The mixture was slowly warmed to room temperature and stirred for 4 hr. At this time, only 50% of the starting material was consumed. The reaction mixture was cooled again to 0° C. To push the reaction to completion, a 3M solution of ethylmagnesium bromide in diethyl ether (50 mL, 150 mmol) was added slowly to the cooled reaction mixture. The reaction was quenched with an aqueous solution of 1N HCl at 0° C. and was extracted with ethyl acetate. The combined organic layer was washed with water and brine. The organic phase was dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The crude material was purified using silica gel column chromatography (100% hexanes ramped to 6% ethyl acetate in hexanes) to give 1-(4-fluoro-2-phenylamino-phenyl)-propan-1-one.

Provenance & Evidence