Citric Acid → 5-Bromo-6-(cyclopropylmethoxy)nicotinic acid

Participants

Reaction Steps

Potassium hydroxide (3.8 g, 51 mmol) was added to a solution of 5-bromo-6-chloro-3-pyridinecarboxylic acid (CAS 29241-62-1; 3 g, 13 mmol) and cyclopropanemethanol (1.5 mL, 19 mmol) in dimethylsulfoxide (12 mL). The mixture was microwaved at 100° C. for 4 min and poured into a mixture of water (50 mL) and citric acid (150 mL, 10%). The precipitating solid was collected by filtration, washed with water, dissolved in ethyl acetate and dried with Na2SO4. The solvent was removed to yield a solid which was stirred with a mixture of heptane/ethylacetate (40 mL, 1:1), filtered, washed with heptane and dried to yield 2.45 g of the title compound as colorless solid, MS (ISP) 270.1, 272.1 (M−H)−.

Provenance & Evidence