Sodium Chloride → 3-(Chlorosulfonyl)-4-fluorobenzoic acid

HRID 1515419Notes

Reaction equation

HRID 1515419 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.[Cl:11][S:12](O)(=[O:14])=[O:13].[Cl-].[Na+]>>[Cl:11][S:12]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:2]=1[F:1])[C:6]([OH:8])=[O:7])(=[O:14])=[O:13]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 99734-Fluorobenzoic AcidHCID 24638Chlorosulfonic acid

Product 1

HCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acidYield 51.5%

Conditions

Temperature
160 °C

Procedure

4-Fluoro-benzoic acid (8 g, 57 mmol) is added carefully to chlorosulfonic acid (58 g, 498 mmol) then sodium chloride (10 g, 169 mmol) is added in small portions. After complete addition, the reaction is heated at 160° C. for 5 h. The reaction mixture is cooled down and poured into ice-water. A white solid precipitate is collected and redissolved in ethyl acetate. The organic layer is washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and the solvent is removed in vacuo. The residue is triturated with hexane to give 7 g (51% yield) of the title compound as a white solid. 1H NMR (CDCl3): δ 8.78 (m, 1H), 8.52 (m, 1H), 7.5 (t, 1H). MS (m/z): 308 (M−1).

Workup

  1. additionAfter complete addition
  2. temperatureThe reaction mixture is cooled down
  3. customA white solid precipitate is collected
  4. dissolutionredissolved in ethyl acetate
  5. washThe organic layer is washed with a saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed in vacuo
  9. customThe residue is triturated with hexane

Sources & evidence

ORD record
ord-b891dd208aa942f5b9270fd98dd0c71b
Source dataset
uspto-grants-2012_07
Patent number
US08222424B2

Reaction notes

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