Hydrazine hydrate (1:1) → (E)-1-(4-bromo-2,5-difluorophenyl)ethylidenehydrazine

HRID 1398617Notes

Reaction equation

HRID 1398617 reaction equation
[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([C:9](=O)[CH3:10])=[C:4]([F:12])[CH:3]=1.O.[NH2:14][NH2:15]>C(O)C>[Br:1][C:2]1[C:7]([F:8])=[CH:6][C:5](/[C:9](=[N:14]/[NH2:15])/[CH3:10])=[C:4]([F:12])[CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 99916531-(4-Bromo-2,5-difluorophenyl)ethan-1-one

Product 1

HCID 88861565(E)-1-(4-bromo-2,5-difluorophenyl)ethylidenehydrazineYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-bromo-2,5-difluorophenyl)ethanone (500 mg, 1.042 mmol) was dissolved in ethanol (10 mL), then hydrazine hydrate (57.4 mg, 1.147 mmol) added and stirred at RT for 16 hr. A pale yellow solid was filtered off and the filtrate was concentrated under reduced pressure to obtain the crude title compound as a brown-yellow solid (249 mg, 54% yield); 1H NMR (500 MHz, CHLOROFORM-d)delta 2.13 (3H, d, J=2.99 Hz), 7.28 (1H, dd, J=9.85, 5.60 Hz), 7.34 (1H, dd, J=9.14, 6.62 Hz).

Workup

  1. filtrationA pale yellow solid was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9d96089b1c08479e817291ccf8f5c8d0
Source dataset
uspto-grants-2014_12
Patent number
US08901313B2

Reaction notes

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