Sodium Carbonate → N-[(4-fluorophenyl)methylidene]hydroxylamine

Participants

Reaction Steps

To a solution of 4-fluorobenzaldehyde (3.0 g, 24.1 mmol) in MeOH (15 mL) was added NH2OH.HCl (2.0 g, 29.1 mmol) and Na2CO3 (1.53 g, 14.4 mmol) and the reaction stirred for 4 hours at room temperature. The reaction was concentrated under reduced pressure, extracted with DCM (2×100 mL), and the organic layer washed with water (2×50 mL) followed by brine solution (2×25 mL). The organic layer was concentrated under reduced pressure to obtain 4-fluorobenzaldehyde oxime [Brain, J. Am. Chem. Soc., 133:949-957 (2011)] as white solid (2 g, 61% yield). 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.55 (dd, 2H), 7.06 (t, 2H).

Provenance & Evidence