Acetic Acid → 3-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acid

HRID 2361761Notes

Reaction equation

HRID 2361761 reaction equation
C([O:3][C:4](=[O:23])[CH:5](C#N)[CH:6]([C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1)C.C(O)(=O)C.S(=O)(=O)(O)O>O>[Br:20][C:17]1[CH:16]=[CH:15][C:14]([CH:6]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[CH2:5][C:4]([OH:23])=[O:3])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 576913973-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester

Product 1

HCID 576913963-(4-Bromo-phenyl)-3-(4-chloro-phenyl)-propionic acidYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-(4-bromo-phenyl)-3-(4-chloro-phenyl)-2-cyano-propionic acid ethyl ester (1.91, 4.87 mmol), acetic acid (10 ml), concentrated sulfuric acid (5 ml) and water (5 ml) were refluxed for 2 hours. Reaction mixture was poured into iced water and extracted with ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and concentrated, the crude product was purified over flash silica chromatography eluting with ethyl acetate/petroleum ether (1:1) to afford the desired product (0.82 g, 50% yield). LC/MS: (PS-A2) Rt 3.39 [M+H]− 338.86.

Workup

  1. temperaturewere refluxed for 2 hours
  2. customReaction mixture
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude product was purified over flash silica chromatography
  9. washeluting with ethyl acetate/petroleum ether (1:1)

Sources & evidence

ORD record
ord-58eedd880e6d4357a34b56a3da192e07
Source dataset
uspto-grants-2014_04
Patent number
US08691806B2

Reaction notes

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