Sodium Cyanide → 3-(5-Bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile

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Reaction Conditions

Reaction Steps

1H-NMR (CDCl3) δ: 3.78 (3H, s), 3.9-4.5 (3H, m), 3.70 (3H, s), 4.3 (2H, m), 6.70-7.80 (8H, m) e) 1.2 g of sodium cyanide was dissolved in 30 ml of dimethyl sulfoxide at a temperature of 90° C. To this was gradually added 18.5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)propyl methanesulfonate, followed by stirring at 80° C. for 1 hour. The resulting reaction solution was mixed with an ethyl acetate/toluene mixture, washed with water, and then dried to distill off the solvent. Crystals thus precipitated were washed with ethanol and dried to obtain 5 g of 3-(5-bromobenzo[b]thien-2-yl)-2-(4-methoxyphenyl)butyronitrile. The same compound was also obtained with a yield of 2 g, by concentrating the ethanol solution resulting from the washing of crystals and subjecting the concentrate to silica gel column chromatography using chloroform as an elution solvent.

Provenance & Evidence