Benzyl mercaptan → 4-Fluorobenzenecarbodithioic acid phenylmethyl ester

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Reaction Steps

A mixture of 4-fluorobenzoic acid (1.40 g), benzyl mercaptan (1.24 g) and phosphorus pentasulfide (4.44 g) in toluene (40 ml) was refluxed for 12 h. A dark red color was developed immediately after heating. After the reaction was complete (as monitored by GC-MS), it was cooled to room temperature and purified by a column chromatography packed with neutral alumina, eluting with benzene. Removal of the solvent by distillation gave the single compound, benzyl-4-fluorodithiobenzoate (1.86 g, 71%). It was further characterized by 1H and 13C-NMR.

Provenance & Evidence