Water → 3-Fluoro-4-(phenyl sulfonyl)benzeneamine

HRID 865759Notes

Reaction equation

HRID 865759 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:15]([O-])=O)[CH:5]=[CH:6][C:7]=1[S:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Mn]([O-])(=O)(=O)=[O:19].[K+].S([O-])([O-])=O.[Na+].[Na+].[OH2:30]>C(O)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(=[O:19])=[O:30]

Participants

6

Reactant 4

HCID 962Water2×HCID 24437Sodium SulfiteHCID 516875Potassium PermanganateHCID 149263253-Fluoro-4-(phenylthio)nitrobenzene

Product 1

HCID 107532343-Fluoro-4-(phenyl sulfonyl)benzeneamineYield 75%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of 3-fluoro-4-(phenylthio)nitrobenzene (5.65 g, 22.7 mmol) in glacial acetic acid (200 mL) was added potassium permanganate (4.30 g, 27.2 mmol) in distilled water (75 mL). The dark brown mixture was stirred at room temperature for 1 hour, then treated with solid sodium sulfite until the solution clarified. The mixture was diluted with water and filtered to yield an off-white solid. Recrystallization from absolute ethanol yielded the title sulfone (4.80 g, 75%) as an off-white solid; mp 124°-125° C. 1H-NMR (300 MHz, DMSO-d6): 7.68-7.73 (m, 2H, aromatic) 7.79-7.84 (m, 1H, aromatic) 8.00 (d, 2H, J=8.2 Hz, aromatic) 8.28-8.38 (m, 3H, aromatic). MS (CI, CH4): 282 (M+1).

Workup

  1. filtrationfiltered
  2. customto yield an off-white solid
  3. customRecrystallization from absolute ethanol

Sources & evidence

ORD record
ord-6c8b3f09ae10464484a464426d6283a4
Source dataset
uspto-grants-1996_10
Patent number
US05567735

Reaction notes

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