Trifluoroacetic acid → 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid

HRID 1522770Notes

Reaction equation

HRID 1522770 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:31])([F:30])[F:29])[S:13][N:12]=[C:11]([C:14]3[CH:26]=[CH:25][C:17]([C:18]([O:20]C(C)(C)C)=[O:19])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:28]([F:30])([F:29])[F:31])[S:13][N:12]=[C:11]([C:14]3[CH:26]=[CH:25][C:17]([C:18]([OH:20])=[O:19])=[C:16]([CH3:27])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89444266tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

Product 1

HCID 894445434-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acidYield 96.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate (164 mg) in dichloromethane (1.7 mL) was added trifluoroacetic acid (0.17 mL). The reaction mixture was stirred at room temperature for 6 hours then the solution was concentrated under vacuo. The residue was extracted with water and ethyl acetate. The organic extract was washed with water, dried over sodium sulfate and concentrated to give 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoic acid (140 mg) as a white foam.

Workup

  1. concentrationthe solution was concentrated under vacuo
  2. extractionThe residue was extracted with water and ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c48a603b651146ff87efa4c8c10a06b8
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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