4-Fluorophenol → 3-(4-Fluorophenoxy)aniline

HRID 29881

Reaction equation

HRID 29881 reaction equation
F[C:2]1[CH:3]=[C:4]([N+:8]([O-])=O)[CH:5]=[CH:6][CH:7]=1.[F:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.C([O-])([O-])=O.[K+].[K+]>CNC>[F:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[CH:6][CH:7]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 98231-Fluoro-3-nitrobenzeneHCID 11430Potassium Carbonate

Product 1

HCID 235060153-(4-Fluorophenoxy)anilineYield 91.2%

Reagents, catalysts & solvents 1

HCID 674DimethylamineSolvent

Procedure

Alternatively, 3-(4-fluoro-phenoxy)-phenylamine was prepared by a two-step procedure by heating a suspension of m-fluoronitrobenzene (4.06 g, 28.7 mmol), p-fluorophenol (3.21 g, 28.6 mmol) and K2CO3 (8.13 g, 58.8 mmol) in DMA (dimethylamine) (60 mL) at 150° C. for 3 hours. The brown reaction mixture was concentrated to one-quarter original volume, diluted with ethyl acetate (220 mL) and washed successively with water (220 mL), 1N NaOH (220 mL) and brine (220 mL). The organic layer was dried (MgSO4) and the solvent removed in vacuo to afford the diphenylether (5.30 g, 80%) as a brown oil.

Workup

  1. customAlternatively, 3-(4-fluoro-phenoxy)-phenylamine was prepared by a two-step procedure
  2. temperatureby heating
  3. concentrationThe brown reaction mixture was concentrated to one-quarter original volume
  4. additiondiluted with ethyl acetate (220 mL)
  5. washwashed successively with water (220 mL), 1N NaOH (220 mL) and brine (220 mL)
  6. dry with materialThe organic layer was dried (MgSO4)
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-2b2c63fa300748dea9d913c55c851a3d
Source dataset
uspto-grants-2008_09
Patent number
US07423043B2

Linked notes

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