Phenylacetyl chloride → Phenylacetyl isothiocyanate

Participants

Reaction Conditions

Reaction Steps

To a 250 mL round bottom flask was added phenylacetylchloride (15.0 g, 97.0 mmol) and toluene (70 mL) followed by lead (II) thiocyanate (25.7 g, 97.0 mmol). Upon completion of addition, the resulting suspension was stirred at 85° C. for 18 h. After this time, the resulting solids were separated by vacuum filtration, and the filtrate was concentrated by rotary evaporation to provide a residue. The residue was purified via silica gel chromatography (10% EtOAc:Hex) to yield the title compound as a pale yellow, non-viscous oil (12.2 g, 68.8 mmol, 71%). 1H NMR (400 MHz, CDCl3): δ ppm 7.41-7.30 (m, 3H), 7.29-7.23 (m, 2H), 3.85 (s, 2H).

Provenance & Evidence