2-Fluoroaniline → 2-Fluoro-4-thiocyanatoaniline

Participants

Reaction Conditions

Reaction Steps

To 550 ml of methanol were added 111 g of 2-fluoroaniline and 240 g of sodium thiocyanate, and the mixture was cooled to 0° C. A cooled (0° C.) solution of 176 g of bromine in 500 ml of methanol saturated with sodium bromide was added dropwise to the mixture, with stirring, over the period of 1 hour 15 minutes, during which cooling was effected to maintain the internal temperature at not more than 3° C. After the addition of bromine was completed, the reaction mixture was poured in 2 l of cold water, and 100 g of sodium hydrogencarbonate was added to make the mixture weakly alkaline. The crystals, which separated out, were recovered by filtration and washed with cold water to give 144.5 g of crude 2-fluoro-4-thiocyanatoaniline.

Provenance & Evidence