Hydrochloric Acid → 1-(5-Bromopyridin-2-YL)cyclopropanecarboxylic acid

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Reaction Steps

A flask charged with a stir bar, 1-(5-bromo-pyridin-2-yl)-cyclopropanecarbonitrile (1.00 g), 25% aqueous NaOH solution (1 mL), and ethanol (10 mL) was heated to 100° C., and the mixture was stirred at this temperature for 14 h. After cooling to room temperature, the solution was poured into ice-cold saturated aqueous Na2HPO4 solution and the resulting mixture was adjusted to pH 4 by the addition of 1 M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was recrystallized from diisopropyl ether to give the title compound as a yellowish solid. Yield: 0.58 g (53% of theory); LC (method 1): tR=0.60 min; Mass spectrum (ESI+): m/z=242/244 (Br) [M+H]+.

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