p-Bromoacetophenone → (4-Bromo-phenyl)-oxo-acetaldehyde oxime

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Reaction Steps

19.9 g of 4-bromoacetophenone are placed in 150 ml of methanol under nitrogen, and 14.7 ml of isopentyl nitrite are added. To the resulting solution there are then added dropwise, at 17-23° C., 22.2 ml of a 5.4M solution of sodium methanolate in methanol. After 70 hours' stirring at room temperature the orange suspension is concentrated using a rotary evaporator. 300 ml of water are added to the residue, and the mixture is rendered acidic with 60 ml of 2N hydrochloric acid. The resulting yellow suspension is filtered and washed with water; the filter cake is taken up in ethyl acetate and washed with water. The organic phase is washed with saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The crude product is recrystallised from ethyl acetate/toluene. In this way (4-bromophenyl)-oxoacetaldehyde oxime is obtained in the form of a colourless powder.

Provenance & Evidence