Dichloromethane → 2-(5-Cyanothien-2-yl)anisole

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Reaction Steps

A solution of 5-bromothiophene-2-carbonitrile (1.25 g, 6.647 mmol) in 50 ml of dioxane is degassed with argon. Tetrakis(triphenylphosphine)palladium(0) (768 mg, 0.665 mmol) is added and the mixture stirred for 5 minutes. 2-Methoxybenzene boronic acid (2.02 g, 13.3 mmol) and 13.3 ml of aqueous 2 N sodium carbonate are successively added and the mixture is stirred for 16 hours at 85° C. Extractive work-up (2×50 ml dichloromethane and 2×30 ml water). Organic phase is dried over sodium sulfate, filtered and evaporated. The residue (4.05 g) is purified via flash column on silica (eluent: 100% hexane>hexane/ethyl acetate 96:4 gradient to give 1.37 g of 2-(5-cyanothien-2-yl)anisole (96%). MS=215 (M+).

Provenance & Evidence