2-Fluorobenzoic acid → 2-Fluoro-5-chlorosulfonylbenzoic acid

HRID 1533438Notes

Reaction equation

HRID 1533438 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[Cl:11][S:12]([C:8]1[CH:9]=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 99352-Fluorobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 6089842-Fluoro-5-chlorosulfonylbenzoic acidYield 78.1%

Conditions

Temperature
90 °C

Procedure

Commercially available 2-fluorobenzoic acid (75 g, 0.54 Mol) was added to chlorosulphonic acid (320 g) over 15 minutes, stirred for 30 minutes then heated to 90° C. for 4½ hrs. Once cool, the reaction was quenched onto ice/water (1.5 kg/324 ml) and granulated for 1 hr. The precipitated product was filtered, water washed and dried at 50° C. under vacuo to give the title compound (99.7 g, 78.1%) as a white solid.

Workup

  1. temperatureOnce cool
  2. customthe reaction was quenched onto ice/water (1.5 kg/324 ml)
  3. waitgranulated for 1 hr
  4. filtrationThe precipitated product was filtered
  5. washwater washed
  6. customdried at 50° C. under vacuo

Sources & evidence

ORD record
ord-88949904a7db4228a3285ce1abda464d
Source dataset
uspto-grants-2001_03
Patent number
US06207829B1

Reaction notes

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