Diphosgene → 4-Fluoro-5-iodo-isatoic Anhydride

HRID 458093Notes

Reaction equation

HRID 458093 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([I:12])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl[C:14]([O:17]C(Cl)=O)(Cl)Cl>O1CCOCC1>[F:11][C:9]1[CH:10]=[C:2]2[NH:1][C:14](=[O:17])[O:6][C:4](=[O:5])[C:3]2=[CH:7][C:8]=1[I:12]

Participants

4

Reactant 2

HCID 10426DiphosgeneHCID 219521462-Amino-4-fluoro-5-iodobenzoic acid

Product 1

HCID 543357764-Fluoro-5-iodo-isatoic AnhydrideYield 90.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Anhydrous dioxane (0.5 liters), 2-amino-4-fluoro-5-iodo-benzoic acid (46 grams, 164 mmoles), and trichloromethylchloroformate (97.4 grams, 492 mmoles) were added to a one liter one neck flask equipped with a magnetic stir bar and reflux condenser. The solution was placed under anhydrous nitrogen, stirred and heated to reflux for 16 hours. The reaction mixture was allowed to cool and was poured into one liter of hexanes. The solid was collected by suction filtration, washed with an additional 0.5 liters of hexanes, and dried under vacuum at room temperature to yield 45.5 grams (90%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ: 11.86 (s, 1H), 8.24 (d, 1H), 6.84 (d, 1H). ESI-MS m/z 308 (M+1).

Workup

  1. customequipped with a magnetic stir bar
  2. temperaturereflux condenser
  3. temperatureheated
  4. temperatureto reflux for 16 hours
  5. temperatureto cool
  6. filtrationThe solid was collected by suction filtration
  7. washwashed with an additional 0.5 liters of hexanes
  8. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-6f2a97c29c20450d83af13862fc0e48d
Source dataset
uspto-grants-2007_03
Patent number
US07189734B2

Reaction notes

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