Trimethylsilyl iodide → 2-Fluoromethyl-2-phthalimido-5-iodopentanenitrile

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Reaction Steps

2-Fluoromethyl-2-phthalimido-5-methoxy-valeronitrile (1.20 g, 4.14 mmol), trimethylsilyl iodide (3.2 g, 16 mmol) and chloroform (15 mL) are heated to 60° C. under nitrogen for 48 hours. After removal of the solvent, the residue is dissolved in chloroform, washed with water, sodium thiosulfate solution and water again, dried and evaporated to give the crude product as an oil (1.2 g). This is purified by chromatography on silica (ethyl acetate/petroleum ether 1:3) to give pure 2-fluoromethyl-2-phthalimido-5-iodo-valeronitrile. NMR (CDCl3) δ: 2.0 (4H, m), 3.10 (2H, t), 4.90 (2H, ABX, JAB =9 Hz, JAX =JBX =JH-F =46 Hz), 7.70 (4H, s).

Provenance & Evidence