Water → 4-(Methylsulfonyl)-3-(trifluoromethyl)aniline

HRID 396800Notes

Reaction equation

HRID 396800 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-])=O)=[CH:7][C:6]=1[C:14]([F:17])([F:16])[F:15])(=[O:4])=[O:3].[Cl-].[NH4+].O>C(O)C.[Fe]>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:6]=1[C:14]([F:15])([F:16])[F:17])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 206051531-(Methylsulphonyl)-4-nitro-2-(trifluoromethyl)benzene

Product 1

HCID 223166824-(Methylsulfonyl)-3-(trifluoromethyl)anilineYield 76.2%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-(methylsulfonyl)-3-(trifluoromethyl)nitrobenzene (1.55 g, 5.76 mmol), iron powder (1.61 g, 28.8 mmol), and ammonium chloride (0.031 g, 0.58 mmol) in ethanol (30 mL), and water (8 mL) was heated at reflux temperature for 1 hour. After cooling, insolubles were filtered off by Celite, and volatiles were removed by evaporation. The residue was redissolved in ethyl acetate (50 mL) and the whole washed with water and brine. After dried over MgSO4 and concentration in vacuo. The residue was washed with hexane to give the subtitle compound (1.05 g, 76.2%, yield).

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 1 hour
  3. temperatureAfter cooling
  4. filtrationinsolubles were filtered off by Celite, and volatiles
  5. customwere removed by evaporation
  6. dissolutionThe residue was redissolved in ethyl acetate (50 mL)
  7. washthe whole washed with water and brine
  8. dry with materialAfter dried over MgSO4 and concentration in vacuo
  9. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-28ca1636ddcf41cc9aa12ad48236b022
Source dataset
uspto-grants-2003_08
Patent number
US06608095B2

Reaction notes

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