HCID 11474735, compound → HCID 11186454, compound

HRID 1369077Notes

Reaction equation

HRID 1369077 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]([O:18]C)=O)([O-])=O>CO>[F:12][C:11]([F:14])([F:13])[C:6]1[CH:7]=[C:8]([I:10])[CH:9]=[C:4]2[C:5]=1[CH2:15][C:16](=[O:18])[NH:1]2

Participants

3

Reactant 1

HCID 11474735HCID 11474735, compound

Product 1

HCID 11186454HCID 11186454, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To methyl [2-nitro-4-iodo-6-(trifluoromethyl)phenyl]acetate (33.11 g, 85.1 mmol) in MeOH (1000 mL) at 0° C. was added aqueous 20% TiCl3 (815 g, 12.4 eq). The cooling bath was removed and the resulting mixture stirred at room temperature for 3 hours and then left overnight. To the mixture was then added aqueous 6N HCl (900 mL) and the mixture extracted with EtOAc:toluene (1:1, 3×1000 mL) and EtOAc:toluene (2:1, 3×900 mL and 3×500 mL). The extracts were combined and dried (anhydrous MgSO4). After filtration, the solvent was removed in vacuo to give a light brown solid. Purification was carried out by crystallization from EtOH (300 mL) to give the title compound as a light brown crystalline solid (21.588 g, 78%).

Workup

  1. customThe cooling bath was removed
  2. waitleft overnight
  3. extractionadded aqueous 6N HCl (900 mL) and the mixture extracted with EtOAc:toluene (1:1, 3×1000 mL) and EtOAc:toluene (2:1, 3×900 mL and 3×500 mL)
  4. dry with materialdried (anhydrous MgSO4)
  5. filtrationAfter filtration
  6. customthe solvent was removed in vacuo
  7. customto give a light brown solid
  8. customPurification
  9. customwas carried out by crystallization from EtOH (300 mL)

Sources & evidence

ORD record
ord-70aeea7337204cd6aeb2f61074393913
Source dataset
uspto-grants-2003_06
Patent number
US06576656B1

Reaction notes

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