Chlorosulfonic acid → 2,4-Difluoro-5-nitrobenzenesulfonyl chloride

HRID 536052Notes

Reaction equation

HRID 536052 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[Cl:12][S:13](O)(=[O:15])=[O:14]>>[F:8][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N+:9]([O-:11])=[O:10])=[CH:4][C:5]=1[S:13]([Cl:12])(=[O:15])=[O:14]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 679672,4-Difluoronitrobenzene

Product 1

HCID 49621612,4-Difluoro-5-nitrobenzenesulfonyl chlorideYield 81%

Conditions

Temperature
100 °C

Procedure

A mixture of 2,4-difluoro-1-nitrobenzene (20 g, 126 mmol) in chlorosulfonic acid (44 g, 378 mmol) was stirred at 100° C. for 48 hours before being poured into ice-water and extracted with EtOAc. The organic extract was dried (Na2SO4) and concentrated, and the residue was triturated with 10% EtOAc-petroleum ether to give 2,4-difluoro-5-nitrobenzenesulfonyl chloride as a brown oil (21 g, 81%) which was used directly in the next step.

Workup

  1. extractionextracted with EtOAc
  2. extractionThe organic extract
  3. dry with materialwas dried (Na2SO4)
  4. concentrationconcentrated
  5. customthe residue was triturated with 10% EtOAc-petroleum ether

Sources & evidence

ORD record
ord-4d29dc274b844d67b1318e46824a7a5b
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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