Benzaldehyde → HCID 19787430, compound

Participants

Reaction Steps

A 50-ml four-neck flask equipped with a dehydrating column was charged with 5-amino-2-chloro-4-fluorophenol (1 g), benzaldehyde (0.68 g), p-toluenesulfonic acid (10 mg) and toluene (50 g). The mixture was dehydrated under reflux under normal pressure for 5 hours, and then concentrated under reduced pressure. The precipitated crystals were filtered and washed with a small amount of hexane to give 1.46 g of 5-benzylidenamino-2-chloro-4-fluorophenol as pale brown needle crystals (yield, 94.5%), m.p., 157°-159° C.; MS (m/z) 249 (M+) 172; NMR (CDCl3, δ): 5.1-5.8 (broad, 1H), 6.83 (d, 1H, J=7.6 Hz), 7.15 (d, 1H, J=9.6 Hz), 7.4-7.6 (m, 3H), 7.8-8.0 (m, 2H), 8.47 (s, 1H).

Provenance & Evidence