Phosgene → 7-Fluoroisatoic anhydride

HRID 1648210Notes

Reaction equation

HRID 1648210 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[C:12](Cl)(Cl)=[O:13]>>[F:11][C:9]1[CH:10]=[C:2]2[NH:1][C:12](=[O:13])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=1

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 100581387-Fluoroisatoic anhydrideYield 100%

Procedure

To a solution of 2-amino-4-fluorobenzoic acid (4.65 g) in 50 mL of mixed solvent (10:1=toluene:tetrahydrofuran) was added phosgene (4.46 g, 1.93M solution of toluene ) dropwise via a drop funnel. The mixture was stirred at room temperature for 1 hour and then heated to reflux over night. The mixture was concentrated to about 10 mL and cooled in refrigerator. The precipitate was filtered, washed with ether (5 mL×2) and air-dried to give the title compound (5.43 g) as a white solid having the following physical data.

Workup

  1. temperatureheated
  2. temperatureto reflux over night
  3. concentrationThe mixture was concentrated to about 10 mL
  4. temperaturecooled in refrigerator
  5. filtrationThe precipitate was filtered
  6. washwashed with ether (5 mL×2)
  7. customair-dried

Sources & evidence

ORD record
ord-37596138178049a883b1a387dac47497
Source dataset
uspto-grants-1995_07
Patent number
US05436233

Reaction notes

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