Trifluoroacetic acid → (5-CHLORO-2-OXO-BENZOOXAZOL-3-YL)-ACETIC ACID

HRID 1428383Notes

Reaction equation

HRID 1428383 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])[C:6]=2[CH:19]=1.C(O)(C(F)(F)F)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8](=[O:10])[N:7]([CH2:11][C:12]([OH:14])=[O:13])[C:6]=2[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 117660476HCID 117660476, compound

Product 1

HCID 3921330(5-CHLORO-2-OXO-BENZOOXAZOL-3-YL)-ACETIC ACIDYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl (5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate (50 g) and dichloromethane (250 mL) was added TFA (67.4 mL), followed by stirring at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and then to the residue was added water. The resulting solid was collected by filtration and then washed with water to obtain (5-chloro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetic acid (38.5 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionto the residue was added water
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-7e05c096cd6d4583b36c176c51bdefe5
Source dataset
uspto-grants-2015_01
Patent number
US08937087B2

Reaction notes

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