Water → N-ethyl-4-fluoroaniline

HRID 865928Notes

Reaction equation

HRID 865928 reaction equation
I[CH2:2][CH3:3].[F:4][C:5]1[CH:11]=[CH:10][C:8]([NH2:9])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:2]([NH:9][C:8]1[CH:10]=[CH:11][C:5]([F:4])=[CH:6][CH:7]=1)[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 97314-FluoroanilineHCID 11430Potassium Carbonate

Product 1

HCID 4962184N-ethyl-4-fluoroaniline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Iodoethane (3.6 ml) was added to a mixture of 4-fluoroaniline (4.26 ml) and potassium carbonate (6.9 g) in dry DMF (100 ml). After 18.5 h at 23°, the resulting suspension was poured into water (400 ml) and extracted with EA (400 ml). The organic extract was washed with water (200 ml) then saturated brine (200 ml), dried and evaporated. The residual oil was chromatographed with 2 to 3 to 4% EA in hexane as eluent to give the title compound (3.667 g) as a yellow oil.

Workup

  1. extractionextracted with EA (400 ml)
  2. extractionThe organic extract
  3. washwas washed with water (200 ml)
  4. dry with materialsaturated brine (200 ml), dried
  5. customevaporated
  6. customThe residual oil was chromatographed with 2 to 3 to 4% EA in hexane as eluent

Sources & evidence

ORD record
ord-f3ee23012faf4bc980a61779569cdba7
Source dataset
uspto-grants-1996_10
Patent number
US05569654

Reaction notes

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