Triphosgene → 6-Fluoroisatoic anhydride

HRID 2279783Notes

Reaction equation

HRID 2279783 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=[O:5].Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[F:11][C:7]1[C:3]2[C:4](=[O:6])[O:5][C:13](=[O:15])[NH:1][C:2]=2[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 5211422-Amino-6-fluorobenzoic acid

Product 1

HCID 27830576-Fluoroisatoic anhydrideYield 175.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2-amino-6-fluorobenzoic acid (8.0 g, 51.6 mmol) in THF (110 mL) was added triphosgene (7.6 g, 25.8 mmol). The resulting suspension was stirred at 50° C. for 12 h. The reaction mixture was cooled to RT and filtered to give 8.2 g of the title compound as a pink solid (87%). 1H NMR (DMSO-d6, 500 MHz) δ=6.95 (d, J=8.5 Hz, 1H), 7.02-7.05 (m, 1H), 7.69-7.72 (m, 1H), 11.85 (brs, 1H).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered

Sources & evidence

ORD record
ord-9b6d06efb61b4e61b8fc3d754d1e6682
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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