2-Fluoroaniline → 2-Fluoro-4-thiocyanatoaniline

Participants

Reaction Conditions

Reaction Steps

To a mixed liquid of 210.9 g of sodium thiocyanate and 200.9 g of methanol was dropped a solution composed of 60.2 g of sodium bromide, 166.6 g of methanol and 163.7 g of bromine over 90 minutes while internal temperature was controlled at −10 to −6° C. To the mixed liquid was dropped 100.0 g of 2-fluoroaniline over 50 minutes while internal temperature was controlled at −10 to −5° C. The resulting mixture was stirred at the same temperature for 3 hours and then was poured into 784 g of water cooled to 0° C. The resulting mixture was neutralized with sodium carbonate and then was extracted twice with 196 g of chloroform. The organic layer was dried over magnesium sulfate and then concentrated, so that 151.9 g of 2-fluoro-4-thiocyanoaniline (Compound S-4) was obtained.

Provenance & Evidence