Hydrochloric Acid → 2-(4-Iodophenyl)-2-methylpropanenitrile

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Reaction Conditions

Reaction Steps

NMP (197 mL, Sigma-Aldrich) was added to a suspension of sodium tert-butoxide (124.0 g, Alfa-Aesar) in THF (197 mL, Univar) under argon. The mixture was cooled to 0° C. and a solution of iodomethane (87.9 mL, Sigma-Aldrich) and 4-iodophenylacetonitrile (78.4 g) in a 50:50 mixture of NMP/THF (173 mL) was added dropwise keeping the internal temperature below 10° C. The mixture was warmed to room temperature and stirred overnight. 2M HCl (930 mL) and toluene (930 mL) were added then the aqueous layer was separated and extracted with toluene (2×465 mL). The combined organics were washed with saturated sodium bicarbonate (930 mL), brine (930 mL), 2M sodium thiosulfate (930 mL), dried (magnesium sulphate) and concentrated in vacuo to a yellow/orange solid. Purification by column chromatography eluting with EtOAc/heptane mixtures gave the title compound as a pale yellow oil. Yield 4.55 g, 1H NMR (400 MHz, CDCl3): δ 7.71 (2H, d, Ar—H), 7.23 (2H, d, Ar—H), 1.70 (6H, s, CH3).

Provenance & Evidence