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

HRID 1936195Notes

Reaction equation

HRID 1936195 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 14.1%

Conditions

Temperature
85 °C

Procedure

2-Fluoronitrobenzene (10.0 g, 70.9 mmol) was added to chlorosulfonic acid (10.0 ml, 150 mmol) at 65° C. After stirring at 85° C. for 18 h, the reaction mixture was cooled to room temperature and poured onto ice chips and extracted with CH2Cl2 (2×250 ml). The combined organic extracts were washed with saturated NaHCO3 solution and dried (MgSO4). Concentration at room temperature and then at 100° C. under high vacuum produced 2.40 g (14%) of the title compound as a yellow oil. 1H-NMR (CDCl3): δ 8.76 (1H, dd, J=2.4, 6.5 Hz), 8.33 (1H, ddd, J=2.4, 3.8, 9.2 Hz), 7.61 (1H, t, J=9.2 Hz). MS (EI): 239 (15, M+), 204 (100).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. additionpoured onto ice chips
  3. extractionextracted with CH2Cl2 (2×250 ml)
  4. washThe combined organic extracts were washed with saturated NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. concentrationConcentration at room temperature

Sources & evidence

ORD record
ord-17d2e7602f69446fa949a9cc0dcaf1a9
Source dataset
uspto-grants-2002_05
Patent number
US06388131B2

Reaction notes

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