Triphosgene → 5-Fluoroisatoic anhydride

HRID 1186088Notes

Reaction equation

HRID 1186088 reaction equation
[F:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.Cl[C:13](Cl)([O:15]C(=O)OC(Cl)(Cl)Cl)Cl>C1COCC1>[F:1][C:2]1[CH:10]=[C:6]2[C:7]([O:9][C:13](=[O:15])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8]

Participants

4

Reactant 2

HCID 94429TriphosgeneHCID 1014122-Amino-5-fluorobenzoic acid

Product 1

HCID 2885605-Fluoroisatoic anhydrideYield 225.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-fluoroanthranilic acid (10.0 g, 65.5 mmol) in THF (143 mL) was added solid triphosgene (6.70 g, 22.6 mmol, 0.35 equiv). The reaction mixture was stirred at rt overnight and the resulting suspension was filtered and dried to afford 9.23 g (79%) of 5-fluoroisatoic anhydride: 1H NMR (400 MHz, DMSO-d6) δ 7.14 (M, 1H), 7.60 (M, 2H), 11.72 (s, 1H).

Workup

  1. filtrationthe resulting suspension was filtered
  2. customdried

Sources & evidence

ORD record
ord-96146f1d9abc457294ba8a25143c1046
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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