Phenylhydrazine → (Z)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine

Participants

Reaction Steps

Into a 500-mL round-bottom flask, was placed a solution of 1-(4-bromo-2-fluorophenyl)ethanone (17 g, 78.34 mmol, 1.00 equiv) in ethanol (200 mL), 1-phenylhydrazine (8.5 g, 78.70 mmol, 1.00 equiv), TSA-H2O (740 mg, 3.89 mmol, 0.05 equiv). The resulting solution was heated to reflux for 2 h in an oil bath, then concentrated under vacuum to yield (Z)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine and (E)-1-(1-(4-bromo-2-fluorophenyl)ethylidene)-2-phenylhydrazine as a yellow solid. MS (m/z): 307 [M+H]+

Provenance & Evidence