Trifluoroacetic acid → HCID 58046327, compound

HRID 2359333Notes

Reaction equation

HRID 2359333 reaction equation
[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:27])([F:26])[F:25])=[C:19]([Cl:28])[CH:18]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([O:9]C(C)(C)C)=[O:8].FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:3]([O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:25])([F:26])[F:27])=[C:19]([Cl:28])[CH:18]=2)=[CH:4][C:5]([F:15])=[C:6]([CH:14]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 58046321HCID 58046321, compound

Product 1

HCID 58046327HCID 58046327, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 5-chloro-4-[3-chloro-4-(trifluoromethoxy)phenoxy]-2-fluorobenzoate (Preparation 161, 41.88 g, 0.0868 mol) was dissolved in dichloromethane (75 mL), then trifluoroacetic acid (21.2 mL, 0.285 mol) was added and the mixture was stirred at room temperature for 50 hours. Trifluoroacetic acid was added again (1.2 mL, 0.017 mol) and the reaction left to stir for 4 hours. A solid was observed in the flask, so it was collected by filtration. The filtrate was concentrated in vacuo and dichloromethane (5 mL) was added to the crude, which was stirred for 5 minutes at room temperature. The resulting solid was collected by filtration and set aside. The crops were combined and title compound was isolated as a white solid (29.6 g, 81%).

Workup

  1. waitthe reaction left
  2. stirringto stir for 4 hours
  3. filtrationwas collected by filtration
  4. concentrationThe filtrate was concentrated in vacuo and dichloromethane (5 mL)
  5. additionwas added to the crude, which
  6. stirringwas stirred for 5 minutes at room temperature
  7. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-75df01c9b4f545fca2ba7299cb20a1c8
Source dataset
uspto-grants-2014_04
Patent number
US08685977B2

Reaction notes

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