2,6-Dichlorobenzoic acid → 2,6-dichloro-3-chlorosulfonyl-benzoic Acid

HRID 1992147Notes

Reaction equation

HRID 1992147 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[C:8]=1[C:9]([OH:11])=[O:10]>>[Cl:6][C:7]1[C:15]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:14][CH:13]=[C:12]([Cl:16])[C:8]=1[C:9]([OH:11])=[O:10]

Participants

3

Reactant 2

HCID 57582,6-Dichlorobenzoic acidHCID 24638Chlorosulfonic acid

Product 1

HCID 35382162,6-dichloro-3-chlorosulfonyl-benzoic AcidYield 85%

Conditions

Temperature
150 °C

Procedure

Chlorosulfonic acid was slowly added to 2,6-dichlorobenzoic acid at RT under N2. The reaction was heated to 150° C. for 3 h, then slowly poured over ice and the product extracted into Et2O. The organic layer was dried over MgSO4, filtered and concentrated to give 2,6-dichloro-3-(chlorosulfonyl)benzoic acid 880-1a as a brown solid (12.9 g, 85% yield).

Workup

  1. additionslowly poured over ice
  2. extractionthe product extracted into Et2O
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9a3c6d223b1d42b1a7256e6ba817d1d2
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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