1,3-Dibromo-5,5-dimethylhydantoin → 6-(Bromomethyl)-3-pyridinecarboxylic acid

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Reaction Steps

1st step: To a stirred suspension of 6-methylnicotinic acid (commercially available) (500 mg, 3.64 mmol) in THF (14 mL) at RT, was added 1,3-dibromo-5,5-dimethylhydantoin (DDH) (1.06 g, 3.71 mmol). Stirring was continued over night and concentrated under vacuo. Column chromatography (SiO2, CH2Cl2/MeOH: 8/2) yielded 410 mg (52%) of 6-bromomethyl-nicotinic acid as a light orange solid. ES-MS m/e: 214.2-216.3 (M+H+).

Provenance & Evidence