Ammonium Chloride → 1400701-89-4

Participants

Reaction Steps

To a solution of 4-bromo-2-chloro-N-methoxy-N-methylbenzamide (synthesized by the method of Bioorganic & Medicinal Chemistry Letters 2003, 13, 3983, 5.90 g, 21.0 mmol) in tetrahydrofuran (180 mL) was added dropwise a solution of 0.7 mol/L cyclopropylmagnesium bromide in tetrahydrofuran (65.0 mL, 45.5 mmol) at 0° C. The mixture was stirred at the same temperature for 4 hours, and then to the reaction solution was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate three times. The organic layer was combined, washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=100:0→93:7) to give (4-bromo-2-chlorophenyl)(cyclopropyl)methanone (3.75 g, 68%) as a pale yellow oil.

Provenance & Evidence