Bromine → Methyl 2-[2-(bromomethyl)phenyl]-2-(methoxyimino)acetate

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Reaction Steps

21.4 g (0.133 mol) of bromine are added, while stirring, to 27.5 g (0.133 mol) of 2-methylphenylglyoxylic acid methyl ester O-methyloxime dissolved in 400 ml of tetrachloromethane. The mixture is then refluxed for four hours while being exposed to a 300 W Hg vapor lamp, after which it is evaporated down, the residue is taken up in ethyl acetate/water and the solution is washed with water, dried with sodium sulfate and evaporated down. The crude product is purified by chromatography over silica gel, using 9:1 cyclohexane/ethyl acetate. 17.4 g (46%) of the abovementioned compound are obtained as an oil.

Provenance & Evidence