Hydrochloric Acid → HCID 73461926, compound

Participants

Reaction Steps

To a solution of 2-chloro-6-fluorobenzaldehyde (15.0 g, 94.6 mmol) and hydroxylamine hydrochloride (7.90 g, 114 mmol) in EtOH (25 ml), H2O (25 ml), and ice (40 g) was added NaOH (19 ml, 50% wt. solution). Ice was added during the addition of the NaOH to maintain the reaction temperature below 40 degrees C. The mixture was stirred at room temperature for 1 h. Ice was added, the pH adjusted to 6 with HCl (2 N), and extracted twice with Et2O. The combined Et2O layers were washed (brine) and dried (MgSO4). Filtration and concentration gave a yellow-brown solid that was recrystallized from Et2O/hexanes to give 2-chloro-5-fluorobenzaldehyde oxime (12.2 g, 74%).

Provenance & Evidence