Water → HCID 86694109, compound

Participants

Reaction Conditions

Reaction Steps

1-(2-chloro-5-fluoropyridin-3-yl)cyclopropanecarbonitrile (intermediate 16, 0.400 g, 2.034 mmol) was dissolved in a mixture of water (6 mL) and concentrated sulfuric acid (6 mL). The reaction was heated at 105° C. and stirred for 3½ hours. The reaction was cooled and ice (˜200 mL) and ethyl acetate (200 mL) were added. The pH was carefully adjusted to about 9 and the phases separated. The organic was discarded and the aqueous was reacidified to about pH 1 using 5 N hydrochloric acid. It was extracted with ethyl acetate (2×300 mL). The combined organic layers were dried with magnesium sulfate and evaporated to dryness under reduced pressure. The crude 1-(2-chloro-5-fluoropyridin-3-yl)cyclopropanecarboxylic acid (0.402 g, 1.864 mmol, 92% yield) was used without further purification.

Provenance & Evidence