HCID 11176292, compound → HCID 11474735, compound

HRID 1369076Notes

Reaction equation

HRID 1369076 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:5]=1[CH2:15][C:16]([OH:18])=[O:17])([O-:3])=[O:2].Cl.[CH3:20]O>>[N+:1]([C:4]1[CH:9]=[C:8]([I:10])[CH:7]=[C:6]([C:11]([F:14])([F:12])[F:13])[C:5]=1[CH2:15][C:16]([O:18][CH3:20])=[O:17])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 11176292HCID 11176292, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 11474735HCID 11474735, compoundYield 92%

Procedure

[2-Nitro-4-iodo-6-(trifluoromethyl)phenyl]acetic acid (34.7 g, 96.2 mmol) was dissolved in HCl/MeOH (300 mL) and the solution was heated at reflux for 4.5 hours. The solvent was removed in vacuo and the resulting oil was dissolved in EtOAc (400 mL). The solution was washed with saturated aqueous NaHCO3 (60 mL, 100 mL and 80 mL) and then dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to yield the title compound (33.11 g, 92%).

Workup

  1. temperaturethe solution was heated
  2. temperatureat reflux for 4.5 hours
  3. customThe solvent was removed in vacuo
  4. dissolutionthe resulting oil was dissolved in EtOAc (400 mL)
  5. washThe solution was washed with saturated aqueous NaHCO3 (60 mL, 100 mL and 80 mL)
  6. dry with materialdried (anhydrous MgSO4)
  7. filtrationAfter filtration
  8. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8fd036d7fc6c4a82a2f7bbf17f2697db
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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