Carbon Disulfide → 4-Bromo-1-isothiocyanato-2-methylbenzene

Participants

Reaction Steps

In 800 ml of pyridine were dissolved 275 ml of carbon disulfide and 93 ml of triethylamine. To the solution was added 125 g of 4-bromo-2-methylaniline. The mixture was stirred at room temperature overnight. Thereto was added 138.5 g of 1,3-dicyclohexylcarbodiimide (DCC). The mixture was stirred overnight. Pyridine was removed by distillation. To the residue was added n-hexane. The resulting precipitate (DC-thiourea) was removed by filtration. The filtrate was concentrated and the residue was purified by a silica gel column chromatography (eluant: n-hexane) to obtain 138 g of 4-bromo-2-methylphenyl isothiocyanate.

Provenance & Evidence