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

HRID 1835997Notes

Reaction equation

HRID 1835997 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 273/275 (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-8c86a98f2f57475ebb8b94cf52dd5caf
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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