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 27.6 g (0.133 mol) of 2-methylphenylglyoxylic acid methyl ester O-methyl oxime dissolved in 400 ml of tetrachloromethane. Refluxing is then carried out for four hours with exposure to a 300 W Hg vapor lamp. Thereafter, the mixture 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 theory) of 2-bromomethylphenylglyoxylic acid methyl ester O-methyl oxime are obtained as an oil.

Provenance & Evidence