4-Chloro-2-fluoro-1-nitrobenzene → 4-Chloro-2-ethoxy-1-nitrobenzene

HRID 419852

Reaction equation

HRID 419852 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8](F)[CH:7]=1>C(O)C>[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[C:8]([O:1][CH2:2][CH3:3])[CH:7]=1

Participants

4

Reactant 2

HCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 2723922Sodium ethoxide

Product 1

HCID 6750644-Chloro-2-ethoxy-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (21% in ethanol, 8.6 mL, 26 mmol) was added dropwise to a solution of 4-chloro-2-fluoronitrobenzene (3 g, 17.1 mmol) in ethanol (20 mL), and once addition was complete the reaction was stirred for a further hour. The mixture was concentrated under reduced pressure, the residue was diluted with ethyl acetate, and the solution was washed with water (×2), then brine. The solution was dried over MgSO4 and evaporated under reduced pressure to afford the title compound as a solid, 3.45 g.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate
  3. washthe solution was washed with water (×2)
  4. dry with materialThe solution was dried over MgSO4
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-0e9fc17755da4f0284979d426a28fa9e
Source dataset
uspto-grants-2012_01
Patent number
US08093400B2

Linked notes

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