Chlorosuccinimide → 4-Bromo-2-fluoro-N-hydroxybenzenecarboximidoyl chloride

Participants

Reaction Steps

N-Chlorosuccinimide (0.075 g) was added to a solution of 4-bromo-2-fluorobenzaldehyde oxime (Intermediate 50) (0.44 g) in DMF (1 ml) then heated for several minutes at 55°. The mixture was allowed to cool to <50° then more N-chlorosuccinimide (0.22 g) was added. After a few minutes the mixture was allowed to cool to room temp. then partitioned between water and ether. The layers were separated, the aqueous layer was re-extracted with ether (×2) and the combined organic extracts were washed with water and brine, dried (MgSO4) and concentrated under vacuum to give a white solid (0.46 g).

Provenance & Evidence