Methylhydrazine → 4-Aminooxymethyl-2-bromo-benzoic acid methyl ester

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To a solution of 2-bromo-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxymethyl)-benzoic acid methyl ester (0.40 g, 1.02 mmol) in methylene chloride (15 mL) cooled to 0° C. was added methyl hydrazine (0.087 g, 1.88 mmol). After a few minutes the ice bath was removed and the mixture was allowed to stir at room temperature for 2 hours. The mixture was filtered and the filtrate was concentrated under reduced pressure. The crude material was purified by flash chromatography through silica gel using ethyl acetate/methylene chloride (0/100 gradient to 6/94) to give 4-aminooxymethyl-2-bromo-benzoic acid methyl ester (0.25 g, 94%) as a colorless oil. 1H NMR (400 MHz, CDCl3); δ 7.79 (d, 1H), 7.66 (s, 1H), 7.32 (d, 1H), 4.67 (s, 2H), 3.92 (s, 3H).

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