(NE)-N-[(2,4-difluorophenyl)methylidene]hydroxylamine

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,4-Difluorobenzaldehyde (2.27 g, 16.0 mmol) and hydroxylamine hydrochloride (6.67 g, 96.0 mmol) were added to EtOH (25 mL) and water (25 mL) along with about 40 g of ice. The mixture was stirred and 50% aqueous NaOH (7.68 g, 96 mmol) was added dropwise. The mixture was stirred at ambient temperature for about 15 min then the solid was collected by filtration, washed with water (10 mL) and dried to give the title compound (1.25 g, 50%): 1H NMR (DMSO-d6) δ 11.58 (d, 1H), 8.18 (s, 1H), 7.78 (m, 1H), 7.33 (m, 1H), 7.14 (m, 1H). The mixture was stirred at ambient temperature for about 15 min the solid was collected by filtration washed with water (10 mL) dried