Water → ethyl (2E)-2-[(2-bromo-4-fluorophenyl)hydrazinylidene]propanoate

HRID 1760591Notes

Reaction equation

HRID 1760591 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N:9]=[N:10][C:11]1(C)[C:16](=O)O[C:14](C)([CH3:18])[O:13][C:12]1=[O:20].[Na].O>C(O)C>[CH2:14]([O:13][C:12](=[O:20])/[C:11](=[N:10]/[NH:9][C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[Br:1])/[CH3:16])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 5360545SodiumHCID 225959235-(2-Bromo-4-fluoro-phenylazo)-2,2,5-trimethyl-[1,3]dioxane-4,6-dione

Product 1

HCID 21014459ethyl (2E)-2-[(2-bromo-4-fluorophenyl)hydrazinylidene]propanoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a cooled (ice-bath) suspension of 126 g 5-(2-Bromo-4-fluoro-phenylazo)-2,2,5-trimethyl-[1,3]dioxane-4,6-dione in 550 ml ethanol was added a solution of 7.8 g sodium in 200 ml ethanol. The mixture was stirred 5 h at room temperature, poured into 200 ml water and the organics extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and evaporated. The resulting orange oil solidified upon drying under vacuum to afford the title compound. Yield:102 g. ISP-MS: m/e 303.2 ([M+H]+).

Workup

  1. temperatureTo a cooled
  2. extractionthe organics extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customupon drying under vacuum

Sources & evidence

ORD record
ord-0535d93eedb04c1aaf9c76d035cbd249
Source dataset
uspto-grants-2005_01
Patent number
US06844345B2

Reaction notes

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