Trifluoroacetic acid → 3-(chlorosulfonyl)-5-fluorobenzoic acid

HRID 2423241Notes

Reaction equation

HRID 2423241 reaction equation
FC(F)(F)C(O)=O.[Cl:8][S:9]([C:12]1[CH:13]=[C:14]([CH:25]=[C:26]([F:28])[CH:27]=1)[C:15]([O:17]CC1C=CC=CC=1)=[O:16])(=[O:11])=[O:10]>>[Cl:8][S:9]([C:12]1[CH:13]=[C:14]([CH:25]=[C:26]([F:28])[CH:27]=1)[C:15]([OH:17])=[O:16])(=[O:10])=[O:11]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86632597HCID 86632597, compound

Product 1

HCID 37487043-(chlorosulfonyl)-5-fluorobenzoic acidYield 82.1%

Procedure

A trifluoroacetic acid (18 mL) solution of benzyl 3-(chlorosulfonyl)-5-fluorobenzoate (2.30 g) was stirred at 60° C. for 18 hours. The oily substance floating on the liquid surface was removed, and the solution part was decanted and evaporated under reduced pressure. Hexane was added to the residue, then this was sonicated for 10 minutes. The resulting solid was collected by filtration to obtain 3-(chlorosulfonyl)-5-fluorobenzoic acid (1.37 g). EI: 238

Workup

  1. customwas removed
  2. customthe solution part was decanted
  3. customevaporated under reduced pressure
  4. additionHexane was added to the residue
  5. customthis was sonicated for 10 minutes
  6. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-1918c54b18684f078d51ca859cc9e109
Source dataset
uspto-grants-2011_06
Patent number
US07960562B2

Reaction notes

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