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

HRID 418772

Reaction equation

HRID 418772 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]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][NH2:22].C([O-])(=O)C.[Na+]>CO>[F:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[NH:21][N:22]=[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 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 129827482,6-Dibromo-4-methylbenzaldehyde

Product 1

HCID 666483952,6-Dibromo-4-methylbenzaldehyde (2,4-difluorophenyl)hydrazoneYield 74.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2,6-Dibromo-4-methylbenzaldehyde (89.5 g, 0.322 mol), (2,4-difluorophenyl)hydrazine hydrochloride (58.25 g, 0.322 mol) and sodium acetate (26.9 g, 0.328 mol) were heated in methanol (1.25 L) at reflux for 3.5 hours. The mixture was cooled and the precipitate was collected by filtration and partitioned between ethyl acetate (750 mL) and water (250 mL). The ethyl acetate layer was combined with a second ethyl acetate extract, washed successively with water and brine, dried over anhydrous sodium sulphate and evaporated under reduced pressure to afford the title compound as an off-white solid (97.5 g).

Workup

  1. temperatureat reflux for 3.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationthe precipitate was collected by filtration
  4. custompartitioned between ethyl acetate (750 mL) and water (250 mL)
  5. extractionextract
  6. washwashed successively with water and brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-e509296f66724446bb0b4bcb87492c90
Source dataset
uspto-grants-2012_01
Patent number
US08093281B2

Linked notes

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