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

HRID 551436Notes

Reaction equation

HRID 551436 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][C:17]([NH:20][NH2:21])=[CH:16][CH:15]=1.C([O-])(=O)C.[Na+]>CO>[F:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][N:21]=[CH:4][C:3]2[C:2]([Br:1])=[CH:9][C:8]([CH3:10])=[CH:7][C:6]=2[Br:11])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 699814-Fluorophenylhydrazine hydrochlorideHCID 517045Sodium AcetateHCID 129827482,6-Dibromo-4-methylbenzaldehyde

Product 1

HCID 666483892,6-Dibromo-4-methylbenzaldehyde (4-fluorophenyl)hydrazoneYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  1. temperatureunder reflux for 2 hours in a nitrogen atmosphere
  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

Sources & evidence

ORD record
ord-1ecb5efe9b31420e8825b43f7630a028
Source dataset
uspto-grants-2011_05
Patent number
US07947727B2

Reaction notes

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