Acetic Acid → 3-Fluoro-4-(methylsulfonyl)aniline

HRID 396767Notes

Reaction equation

HRID 396767 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N+:12]([O-])=O)[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].C(O)(=O)C>O.[Fe]>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9])[NH2:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 223167812-Fluoro-1-(methylsulfonyl)-4-nitrobenzene

Product 1

HCID 223166093-Fluoro-4-(methylsulfonyl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-fluoro-4-(methylsulfonyl)nitrobenzene (8 g, 36.5 mmol), iron powder (22 g, 394 mmol), and acetic acid (0.3 mL) in water (200 mL) was heated at 95° C. for 3 hours. After cooling, insolubles were filtered off by Celite. The filtrate was extracted with ethyl acetate (200 mL×2), the combined organic layer washed with water, brine, dried over MgSO4, and concentrated in vacuo. Chromatographic purification of the residue eluting with ethyl acetate/hexane (1/1) provided the subtitle compound (6.2 g, 90% yield).

Workup

  1. temperatureAfter cooling
  2. filtrationinsolubles were filtered off by Celite
  3. extractionThe filtrate was extracted with ethyl acetate (200 mL×2)
  4. washthe combined organic layer washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue
  8. washeluting with ethyl acetate/hexane (1/1)

Sources & evidence

ORD record
ord-ad14a11c528642279f3d894b74184ebc
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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