Water → 2-Fluoro-n-(2-nitrophenyl)aniline

HRID 1081262Notes

Reaction equation

HRID 1081262 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].O.F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]>[Cu]I>[F:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH:4][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 962WaterHCID 95842-FluoroanilineHCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzene

Product 1

HCID 2613812-Fluoro-n-(2-nitrophenyl)aniline

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

A mixture of 2-fluoroaniline (5.0 g), potassium carbonate (2.5 g) and copper(I)iodide (414 mg) in 2-fluoronitrobenzene (16.9 ml) was heated to 180° under nitrogen for 18 h. The cooled mixture was poured into water (300 ml) and extracted with ethyl acetate (2×250 ml) then the combined extracts were washed with saturated brine and evaporated. The residual brown oil was azeotroped with ethanol/water then toluene. The residue was chromatographed with hexane-DE (100:0 to 95:5) to give the title compound (3.25 g) as a bright orange solid, m.p.58°-9°.

Workup

  1. temperaturewas heated to 180° under nitrogen for 18 h
  2. extractionextracted with ethyl acetate (2×250 ml)
  3. washthe combined extracts were washed with saturated brine
  4. customevaporated
  5. customThe residual brown oil was azeotroped with ethanol/water
  6. customThe residue was chromatographed with hexane-

Sources & evidence

ORD record
ord-6d09095ff529473ea1f7d148863cbfd3
Source dataset
uspto-grants-1996_12
Patent number
US05585376

Reaction notes

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