p-Fluoronitrobenzene → 1-Fluoro-2-(4-nitrophenoxy)benzene

HRID 1851006Notes

Reaction equation

HRID 1851006 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[H-].[Na+].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>CN(C)C=O.Cl[Cu]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1

Participants

6

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 97072-FluorophenolHCID 24758Sodium hydride

Product 1

HCID 579749991-Fluoro-2-(4-nitrophenoxy)benzeneYield 36.7%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Into a 100 mL 3-necked round-bottom flask, was placed a solution of 2-fluorophenol (2.6 g, 23.19 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL) and CuCl (2.2 g, 2.41 equiv). This was followed by the addition of sodium hydride (1.34 g, 55.83 mmol, 0.86 equiv) in portions and then 1-fluoro-4-nitrobenzene (2.8 g, 19.84 mmol, 0.67 equiv). The resulting solution was stirred for 5 h at 100° C. in an oil bath and the resulting solution was diluted with water/ice. The aqueous mixture was extracted with ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate, and concentrated under vacuum. The residue was loaded onto a silica gel column and elution with ethyl acetate/petroleum ether (1:100) gave 1.7 g (31%) of 1-(2-fluorophenoxy)-4-nitrobenzene as a light yellow solid.

Workup

  1. customInto a 100 mL 3-necked round-bottom flask, was placed
  2. extractionThe aqueous mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washThe residue was loaded onto a silica gel column and elution with ethyl acetate/petroleum ether (1:100)

Sources & evidence

ORD record
ord-1ddf32d9f7e5475984c0e1436100d6ca
Source dataset
uspto-grants-2015_02
Patent number
US08957080B2

Reaction notes

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