Toluene → 7-Fluoroisatoic anhydride

HRID 1045976Notes

Reaction equation

HRID 1045976 reaction equation
[C:1](=O)(OC(Cl)(Cl)Cl)[O:2]C(Cl)(Cl)Cl.[NH2:13][C:14]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=[O:17].[OH-].[Na+].C1(C)C=CC=CC=1>O>[F:23][C:21]1[CH:20]=[CH:19][C:15]2[C:16](=[O:18])[O:17][C:1](=[O:2])[NH:13][C:14]=2[CH:22]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 94429TriphosgeneHCID 27249674-Fluoroanthranilic acid

Product 1

HCID 100581387-Fluoroisatoic anhydrideYield 56.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Bis(trichloromethyl) carbonate (3.73 g, 12.57 mmol) was added to a solution of 2-amino-4-fluorobenzoic acid (1.3 g, 8.38 mmol) in sodium hydroxide (2N in water) (8.80 mL, 17.60 mmol) and water (9 mL) at room temperature. The resulting suspension was stirred for 15 minutes then toluene (9.00 mL) was added. The mixture was stirred at room temperature for 18 hours. The resulting precipitate was collected by filtration, washed with water, followed by 20% acetronitrile in Et2O (10 mL) and dried under vacuum at 40° C. to afford 7-fluoro-1H-3,1-benzoxazine-2,4-dione (0.852 g, 56.1%) as a off-white solid.

Workup

  1. stirringThe mixture was stirred at room temperature for 18 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum at 40° C.

Sources & evidence

ORD record
ord-98b72ea7e95441feb943adc7cf93decc
Source dataset
uspto-grants-2013_10
Patent number
US08569298B2

Reaction notes

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