Hydrochloric Acid → 1-(3-Chloropyridin-2-yl)-2-methylpropan-1-one

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Reaction Steps

Chloro(isopropyl)magnesium in THF (35.0 mL, 0.070 mol) was added dropwise to a solution of chloro-2-pyridinecarbonitrile (5.01 g, 0.036 mol) in THF (100 mL) under nitrogen atmosphere at 0° C. It was kept at 0° C. for 2 hours after the addition was complete. The reaction mixture was poured into ice (100 g) and then acidified to pH=3 with an aqueous solution of hydrochloric acid (2.0 M, 100 mL). The product was then extracted with EtOAc (3×100 mL). The organics were combined, dried over sodium sulfate, filtered, and concentrated in vacuo. The resulting crude was purified by silica gel chromatography eluting with 3 to 10% EtOAc in heptane to yield the title compound as a yellow oil (1.98 g, 15% yield):

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