Ammonium Chloride → 3-(4-Bromophenyl)propionic acid

HRID 1264359Notes

Reaction equation

HRID 1264359 reaction equation
[Br:1][C:2]1[CH:12]=[CH:11][C:5]([CH:6]=[CH:7][C:8]([OH:10])=[O:9])=[CH:4][CH:3]=1.[Cl-].[NH4+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][C:8]([OH:10])=[O:9])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 99777p-Bromocinnamic acid

Product 1

HCID 27356093-(4-Bromophenyl)propionic acidYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under nitrogen atmosphere in a 250 mL round bottomed flask containing 4-bromocinnamic acid (5.0 g, 22 mmoles) in 45 mL of N,N-dimethylformamide (0.5 M) was added benzenesulfonylhydrazide (7.6 g, 44 mmoles). The mixture was stirred at reflux for 12 hours. The solution was cooled at room temperature, aqueous saturated ammonium chloride was added and the aqueous layer was extracted with ethyl acetate 3 times. Combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuo. The resulting solid was purified by flash chromatography eluting with 5% methanol:95% dichloromethane to afford 3.66 g (73%) of beige solid.

Workup

  1. temperatureat reflux for 12 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate 3 times
  3. washCombined organic layers were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo
  7. customThe resulting solid was purified by flash chromatography
  8. washeluting with 5% methanol

Sources & evidence

ORD record
ord-b043851cbc0844948e300d06f6d4dfe6
Source dataset
uspto-grants-2003_04
Patent number
US06541661B1

Reaction notes

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