4-Fluorophenylhydrazine hydrochloride → 2,6-Dibromo-4-methylbenzaldehyde (4-fluorophenyl)hydrazone

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Reaction Steps

2,6-Dibromo-4-methylbenzaldehyde (600 g, 2.16 mmol) (which may be prepared according to the method of Lulinski and Serwatowski, Journal of Organic Chemistry, 68, (2003), 5384), (4-fluorophenyl)hydrazine hydrochloride (351 mg, 2.16 mmol) and sodium acetate (180 mg, 2.19 mmol) were heated in methanol (15 ml) under reflux for 2 hours in a nitrogen atmosphere. The methanol was evaporated and the residue partitioned between dichloromethane (30 ml) and aqueous brine (30 ml). The organic phase was separated, combined with additional dichloromethane extracts (2×15 ml), washed with aqueous sodium bicarbonate (2×15 ml), passed through a hydrophobic frit and evaporated to give the title compound (809 mg).

Provenance & Evidence