664364-16-3

92616-49-4

General procedure for the synthesis of 4-bromo-1-naphthalenecarbonitrile (V) from 4-bromo-1-naphthalenecarboxaldehyde oxime (IV): 141 g of the crude product of 4-bromo-1-naphthalenecarboxaldehyde oxime (IV) was added to a 3L reaction flask with 22.6 g of copper acetate monohydrate and 1137 g of acetonitrile, heated to 79 °C and refluxed overnight. The progress of the reaction was monitored by thin layer chromatography (TLC). After completion of the reaction, it was cooled to room temperature and the acetonitrile was removed by distillation under reduced pressure. To the residue, 1500 g of water was added and extracted with 1000 g of dichloromethane. The aqueous phase was extracted twice more with 500 g of dichloromethane and all organic phases were combined. The organic phase was washed with 1500 g of saturated sodium chloride solution. A desiccant was added and stirred and dried overnight. The desiccant was removed by filtration and the filtrate was rotary evaporated at 40°C to remove the solvent. Purification by short column chromatography using dichloromethane as eluent gave 124.3 g of 4-bromo-1-naphthalenecarbonitrile (V). The overall two-step yield based on 4-bromo-1-naphthalenecarboxaldehyde was 94.7% and the purity of the product was 99.3%. Among them, the molar ratio of 4-bromo-1-naphthaldehyde (IV) to copper acetate monohydrate was 1:0.2.