Water → 1-[(4-Fluorophenyl)carbamoyl]cyclopropanecarboxylic Acid

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Reaction Steps

Methyl 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylate (3.28 g, 14.00 mmol) was dissolved in THF (23.34 mL), water (11.67 mL) was added, followed by lithium hydroxide monohydrate (1.763 g, 42.0 mmol), and the mixture stirred at room temperature for 30 minutes. After this time the THF was removed under reduced pressure and the pH of the water layer was adjusted to ˜5 with 2 M HCl while the solution was cooled in an ice bath. The precipitate that formed was dissolved in ethyl acetate (125 mL) and the layers were separated. The organic layer was washed with water (100 mL) and brine (100 mL) and then dried over magnesium sulfate. Evaporation of the solvent yielded 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylic acid (2.952 g, 94% yield) as an off white powder. 1H NMR (400 MHz, DMSO-d6): δ 13.06 (broad s, 1H), 10.56 (s, 1H), 7.60 (m, 2H), 7.12 (m, 2H), 1.39 (s, 4H); MS (ESI) m/z: 224.1 (M+H+).

Provenance & Evidence