Acetic Acid → (3-Bromo-2,5-dimethoxy-phenyl)-acetic acid

HRID 1794494Notes

Reaction equation

HRID 1794494 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4](CC#N)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.[CH3:15][C:16]([OH:18])=[O:17]>O.OS(O)(=O)=O>[Br:1][C:2]1[C:3]([O:13][CH3:14])=[C:4]([CH2:15][C:16]([OH:18])=[O:17])[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 10149238(3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile

Product 1

HCID 10125382(3-Bromo-2,5-dimethoxy-phenyl)-acetic acidYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1118Sulfuric AcidSolvent

Procedure

A solution of (3-Bromo-2,5-dimethoxy-phenyl)-acetonitrile 54 (5.2 g, 20.4 mmol) in water (10 ml), conc H2SO4 (10 ml), and AcOH (30 ml) was heated to 100° C. After 3 hr the reaction was cooled; and poured into water. The aqueous layer was extracted with EtOAc which was then dried over MgSO4, filtered and concentrated. The product was purified by column chromatography on silica gel (50% EtOAc/Hex) to give a solid (2.8 g, 55%): Mp=62–65° C.; 1H NMR (DMSO-d6) δ 12.45 (br s, 1 H), 7.09 (d, 1 H, J=2.9 Hz), 6.87 (d, 1 H, J=3.0 Hz), 3.72 (s, 3 H), 3.66 (s, 3 H), 3.59 (s, 2 H); MS 273/27 (M−H)−.

Workup

  1. temperatureAfter 3 hr the reaction was cooled
  2. extractionThe aqueous layer was extracted with EtOAc which
  3. dry with materialwas then dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography on silica gel (50% EtOAc/Hex)

Sources & evidence

ORD record
ord-9151dc9db81e46da9cc46b27f8c3da9d
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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