Chlorosuccinimide → 2,6-Dichloro-benzaldehyde chloro-oxime

Participants

Reaction Conditions

Reaction Steps

N-Chlorosuccinimide (1162 g, 8.53 mol) in DMF (4.5 L) is added dropwise over a solution of 2,6-dichloro-benzaldehyde oxime (1621.78 g, 8.53 mol) in DMF (5.3 L) heated at 40° C. (addition is complete in about 6 hours). The mixture is stirred for 1 h at that temperature. The reaction is cooled at room temperature, poured onto H2O (30 L) at 0° C., and extracted with MTBE (36 L). The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated to dryness (at 30° C.). The crude, as a solid-oil, is triturated in 1 L of hexane and the solid formed is filtered and dried under vacuum to obtain the desired compound (1440.9 g, 75% yield). MS (m/e): 224 (M+1)

Provenance & Evidence