Chlorosuccinimide → 4-fluoro-N-hydroxybenzenecarboximidoyl chloride

Participants

Reaction Conditions

Reaction Steps

N-Chlorosuccinimide (85.5 g, 438 mmol) was added to a solution of 4-fluorobenzaldehyde oxime (61.0 g, 438 mmol) in DMF (100 mL) at room temperature; an exotherm occurred. After the addition, the solution was heated at 40° C. for 30 minutes under nitrogen. The solution was poured onto ice and extracted with chloroform. The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure, and further dried under high vacuum for 16 hours to provide 52.23 g of 4-fluoro-N-hydroxybenzenecarboximidoyl chloride as an amber oil.

Provenance & Evidence