4-Bromo-2-fluoroaniline → 4-Amino-3-fluorobenzonitrile

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Reaction Steps

50 g (0.26 mol) of 4-bromo-2-fluoroaniline and 30 g (0.34 mol) of CuCN were dissolved in 130 cm3 of NMP and the solution was refluxed with a mantle heater for 2 hours. The reaction solution was cooled to room temperature. 42 cm3 of EDA was added to the cooled solution and the solution was poured into 300 cm3 of ice water. The resulting mixture was extracted with chloroform and washed with an aqueous EDA solution and water. The chloroform was distilled off the washed mixture. The distillation residue was dissolved in ether and washed with water to remove the NMP. The residue was distilled in a vacuum (b.p. 165° C./23 mmHg) to yield 28 g (0.21 mol) of 4-amino-3-fluorobenzonitrile. It was necessary to perform the distillation under an elevated degree of vacuum since the product was extremely sublimable and the crystals adhered to the output of the distillation tube and clogged the tube.

Provenance & Evidence