Sodium Acetate → 2,6-Dibromo-4-methylbenzaldehyde (2-fluorophenyl)hydrazone

HRID 418782

Reaction equation

HRID 418782 reaction equation
[Br:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[C:6]([Br:11])[C:3]=1[CH:4]=O.Cl.[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21].C([O-])(=O)C.[Na+]>CO>[F:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][N:21]=[CH:4][C:3]1[C:2]([Br:1])=[CH:9][C:8]([CH3:10])=[CH:7][C:6]=1[Br:11]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 2723910Hydrazine, (2-fluorophenyl)-, hydrochloride (1:1)HCID 129827482,6-Dibromo-4-methylbenzaldehyde

Product 1

HCID 666488172,6-Dibromo-4-methylbenzaldehyde (2-fluorophenyl)hydrazone

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-Dibromo-4-methylbenzaldehyde (600 g, 2.16 mmol), (2-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. 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 the title compound (767 mg).

Workup

  1. temperatureunder reflux for 2 hours
  2. customThe methanol was evaporated
  3. customthe residue partitioned between dichloromethane (30 mL) and aqueous brine (30 mL)
  4. customThe organic phase was separated
  5. washwashed with aqueous sodium bicarbonate (2×15 mL)
  6. customevaporated to the title compound (767 mg)

Sources & evidence

ORD record
ord-ab513c41dbb045889368f01cd92e690b
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Linked notes

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