Chlorosulfonic acid → 5-(Chlorosulfonyl)-2,4-difluorobenzoic acid

HRID 1992155Notes

Reaction equation

HRID 1992155 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Cl:12][S:13]([C:8]1[C:9]([F:11])=[CH:10][C:2]([F:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 741022,4-Difluorobenzoic acid

Product 1

HCID 107535965-(Chlorosulfonyl)-2,4-difluorobenzoic acidYield 94%

Conditions

Temperature
155 °C

Procedure

A mixture of chlorosulfonic acid (200 mL) and 2,4-difluorobenzoic acid (40 g, 253 mmol, 1 equiv) was heated to 155° C. for 3 h. The reaction was cooled to RT and poured slowly over ice. The product was extracted into ether and the organics dried over MgSO4, filtered and concentrated to give 5-(chlorosulfonyl)-2,4-difluorobenzoic acid 6a as brown solid (61 g, 94% yield).

Workup

  1. temperatureThe reaction was cooled to RT
  2. additionpoured slowly over ice
  3. extractionThe product was extracted into ether
  4. dry with materialthe organics dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ff797023f0be4a51a59d0ce77d2a1b7d
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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