Carbon Disulfide → 3-Fluorobenzyl isothiocyanate

Participants

Reaction Conditions

Reaction Steps

A solution of 3-fluorobenzylamine (6.26 g., 0.05 mole) in ether (10 ml.) was added dropwise to a solution of dicyclohexylcarbodiimide (10.3 g., 0.05 mole) and carbon disulfide (20 ml., 0.333 mole) in ether (60 ml.) at -5 °to -10° C. and the mixture was stirred for 17 hours at 25° C. The mixture was filtered, and the solvent was removed under vacuum. The resulting oil was dissolved in hexane-ethyl acetate (19:1), filtered and the solvent removed under vacuum. The oil was then dissolved in hexane-ethyl acetate (9:1) and purified by flash chromatography (silica) to give 3-fluorobenzylisothiocyanate as an oil (8.14 g., 97%).

Provenance & Evidence