Chlorosulfonic acid → 4-Fluoro-3-nitrobenzene-1-sulfonyl chloride

HRID 536038Notes

Reaction equation

HRID 536038 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[Cl:11][S:12](O)(=[O:14])=[O:13]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:12]([Cl:11])(=[O:14])=[O:13])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 27827994-Fluoro-3-nitrobenzene-1-sulfonyl chlorideYield 65.2%

Conditions

Temperature
100 °C

Procedure

1-Fluoro-2-nitrobenzene (50.0 g, 0.354 mol) was added to chlorosulfonic acid (91 g, 0.778 mol) at 65° C. The resulting mixture was then heated to 100° C. for 18 h. The mixture was cooled to room temperature, poured over ice and extracted with methylene chloride. The combined organic layers were then washed with NaHCO3, then brine, dried over MgSO4, filtered and concentrated in vacuo to afford 4-fluoro-3-nitrobenzenesulfonyl chloride (55.3 g, 65% yield) as a brown oil.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured over ice
  3. extractionextracted with methylene chloride
  4. washThe combined organic layers were then washed with NaHCO3
  5. dry with materialbrine, dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fce13f43402a4465bb523d41adb2d818
Source dataset
uspto-grants-2014_10
Patent number
US08859571B2

Reaction notes

Loading…