4-Fluoroaniline → METHYL 1-[(4-FLUOROPHENYL)CARBAMOYL]CYCLOPROPANECARBOXYLATE

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Reaction Steps

Cyclopropane-1,1-dicarboxylic acid monomethylester (2 g, 13.88 mmol) was dissolved in DMF (28 mL) and 4-fluoroaniline (1.999 mL, 20.82 mmol) was added, followed by diisopropylethylamine (12.12 mL, 69.4 mmol) and O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (8.91 g, 27.8 mmol). The mixture stirred at room temperature for 15 hours and was then diluted with ethyl acetate (200 mL) and washed with 10% aqueous lithium chloride (3×100 mL) and brine (100 mL). The organic layer was dried over magnesium sulfate and evaporated to yield the crude product as a brown solid. It was purified by silica gel chromatography (0 to 20% ethyl acetate/hexane) to give methyl 1-((4-fluorophenyl)carbamoyl)cyclopropanecarboxylate (3.28 g, 99% yield) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 10.32 (s, 1H), 7.60 (m, 2H), 7.12 (m, 2H)), 3.66 (s, 3H), 1.38 (m, 4H); MS (ESI) m/z: 238.1 (M+H+).

Provenance & Evidence