p-Fluoronitrobenzene → 2-Fluoro-5-nitrobenzene-1-sulfonyl chloride

HRID 536050Notes

Reaction equation

HRID 536050 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[Cl:11][S:12](O)(=[O:14])=[O:13]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[S:12]([Cl:11])(=[O:14])=[O:13]

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 24638Chlorosulfonic acid

Product 1

HCID 129043722-Fluoro-5-nitrobenzene-1-sulfonyl chlorideYield 63%

Conditions

Temperature
95 °C

Procedure

A mixture of 1-fluoro-4-nitrobenzene (3.0 g, 21.3 mmol) in chlorosulfonic acid (5.5 mL, 84 mmol) was stirred at 90-100° C. for 8 hours before being cooled to room temperature and slowly poured into ice water and extracted with EtOAc. The organic extract was washed with saturated aq. NaHCO3 and water, dried (sodium sulfate), and concentrated to give 2-fluoro-5-nitrobenzenesulfonyl chloride (3.2 g, 63%) as a colorless oil, which was used directly in the next step.

Workup

  1. temperaturebefore being cooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with saturated aq. NaHCO3 and water
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bae039124b7e42a6b535f3a6dd1a8ffb
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

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