2-Fluoro-4-nitrothioanisole → HCID 22592496, compound

HRID 1931562Notes

Reaction equation

HRID 1931562 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11][CH3:12]>C(O)(=O)C.O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[S:11][CH3:12]

Participants

5

Reactant 1

HCID 225925052-Fluoro-4-nitrothioanisole

Product 1

HCID 22592496HCID 22592496, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Iron (33 g, 0.59 mol) was added to 2-fluoro-1-methylsulfanyl-4-nitro-benzene (18.5 g, 99 mmol) in a mixture of acetic acid (350 mL) and water (70 mL). The mixture was stirred for 2 h with periodic swirling, and then the solvents were evaporated. Ethyl acetate and aqueous sodium bicarbonate solution were added and the mixture was filtered through Celite. The aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with brine, dried (sodium sulfate), filtered, evaporated, and purified by column chromatography, eluting with 20% ethyl acetate/hexanes to give 3-fluoro-4-methylsulfanyl-phenylamine (15.1 g, 97%).

Workup

  1. customthe solvents were evaporated
  2. additionEthyl acetate and aqueous sodium bicarbonate solution were added
  3. filtrationthe mixture was filtered through Celite
  4. extractionThe aqueous layer was extracted three times with ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (sodium sulfate)
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by column chromatography
  10. washeluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3e72f158f2aa48c08d61ade03e517c34
Source dataset
uspto-grants-2012_05
Patent number
US08188098B2

Reaction notes

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