Isopropyl iodide → alpha-Isopropylbenzo(b)thiophene-5-acetonitrile

Participants

Reaction Steps

2-Iodopropane (5.10 g, 0.03 mol) was added to a well stirred mixture of benzo(b)thiophene-5-acetonitrile (2.62 g, 0.015 mol), tetrabutylammonium hydrogen sulphate (5.10 g, 0.015 mol), sodium hydroxide (47% w/w, 1.72 cm3, 0.03 mol) and the mixture was refluxed for 6 hr. with vigorous stirring. The organic layer was washed with water, dried (Na2SO4), filtered and the solvent was removed. The residue was chromatographed on silica using toluene as the eluant and the component with RF 0.52 was isolated as α-isopropylbenzo(b)thiophene-5-acetonitrile (2.00 g, 0.0093 mol, 61.9%).

Provenance & Evidence