Ethyl Acetate → 1-(4-Fluorophenoxy)-2-nitrobenzene

HRID 17734

Reaction equation

HRID 17734 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:17][C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=1.CCOC(C)=O>CN(C=O)C>[F:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][C:6]2[CH:7]=[CH:2][CH:3]=[CH:4][C:5]=2[N+:8]([O-:10])=[O:9])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 9590p-FluoronitrobenzeneHCID 97324-FluorophenolHCID 11430Potassium Carbonate

Product 1

HCID 9611271-(4-Fluorophenoxy)-2-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 1-fluoro-4-nitrobenzene (10 mmol) in DMF (20 mL) at rt, solid potassium carbonate (30 mmol) was added followed by addition of 4-fluorophenol (10 mmol) to the reaction mixture and heating to 80° C. until the reaction was complete as indicated by TLC or HPLC. After cooling to rt, the reaction mixture was poured into EtOAc (100 mL), washed with H2O (2×50 mL) and brine (50 mL), and dried over sodium sulfate. The solvent was removed in vacuuo to afford the desired 4-fluorophenoxy-1-nitrobenzene. The crude product may be used for further transformation.

Workup

  1. temperatureAfter cooling to rt
  2. washwashed with H2O (2×50 mL) and brine (50 mL)
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed in vacuuo

Sources & evidence

ORD record
ord-b7e95b37aff74c7da58bf91ff97b660b
Source dataset
uspto-grants-2010_06
Patent number
US07737285B2

Linked notes

Loading…