Water → Cyano(phenyl)methyl benzenecarbodithioate

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Reaction Steps

To a 100 ml round bottom flask was added 5 ml phenyl magnesium bromide (3M solution in ethyl ether) and diluted to 20 ml with anhydrous THF. 1.2 g carbon disulfide was added dropwise to this mixture and stirred for ½ h at room temperature. Then to the dark red solution was added 3 g α-bromobenzeneacetonitrile dropwise and the mixture stirred for another 3 h. Water was added to the mixture and the organic product was extracted with diethyl ether (3×50 ml), dried with magnesium sulfate overnight and filtered. After removal of solvent and column chromatography (3:1 mixture of hexane and ethyl ether), pure α-cyanobenzyl dithiobenzoate was obtained as a red odorless solid (77% yield). Proton and carbon NMR spectra were consistent with the expected structure, CTA-CP-1.

Provenance & Evidence