Water → Isopropyl (1,3-dithiol-2-ylidene)-(4-fluorophenyl)-acetate

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Reaction Steps

Sodium hydride (2.2 g, 55 % dispersion in mineral oil) is added to a solution of isopropyl 4-fluorophenylacetate (3.9 g) in dry tetrahydrofuran (50 ml). The mixture is stirred for two hours at room temperature. 2-Methylthio-1,3-dithiolium perchlorate (5.5 g) is then added and the mixture is heated under reflux for seven hours. After cooling to room temperature, water (300 ml) is slowly added. The solution is extracted with ether (3×200 ml). The combined organic solutions are washed with water (100 ml), dried over magnesium sulphate and the solvents are evaporated in vacuo. The residue is purified by column chromatography on silica gel using hexane/toluene 1:9 as eluant. The product is recrystallized from ligroin and dried -in vacuo to constant weight to yield isopropyl (1,3-dithiol-2-ylidene)-(4-fluorophenyl)-acetate, m.p. 86° (as Example 8).

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