Chlorosulfonic acid → 3-Bromo-4-fluoro-5-(chlorosulfonyl)benzoic acid

HRID 909389Notes

Reaction equation

HRID 909389 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[F:11])[C:5]([OH:7])=[O:6].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([S:13]([Cl:12])(=[O:15])=[O:14])[C:10]=1[F:11])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 705093-Bromo-4-fluorobenzoic acid

Product 1

HCID 509984803-Bromo-4-fluoro-5-(chlorosulfonyl)benzoic acid

Conditions

Temperature
170 °C

Procedure

3-Bromo-4-fluoro-benzoic acid (2.0 g) was dissolved in chlorosulfonic acid (97%, 35 ml) and heated at 170° C. for 72 h. The reaction mixture was cooled to RT and added dropwise to an ice-water mixture. Extraction with EtOAc, drying (MgSO4) and concentration in vacuo gave the desired compound. Yield: 2.5 g.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionExtraction with EtOAc
  3. customdrying
  4. concentration(MgSO4) and concentration in vacuo

Sources & evidence

ORD record
ord-c23664391d7b449785c805f2ed21d0e8
Source dataset
uspto-grants-2011_09
Patent number
US08017782B2

Reaction notes

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