p-Fluoronitrobenzene → 1-Methyl-4-(methyloxy)-2-[(4-nitrophenyl)oxy]benzene

HRID 1505309Notes

Reaction equation

HRID 1505309 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[OH:10].F[C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[O:10][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 109535825-Methoxy-2-methylphenol2×

Product 1

HCID 672359211-Methyl-4-(methyloxy)-2-[(4-nitrophenyl)oxy]benzeneYield 96.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2-methyl-5-(methyloxy)phenol (Intermediate 12, 1.5 g) and 1-fluoro-4-nitrobenzene (1.4 g, 10.0 mmol) in acetonitrile (100 mL) was added potassium carbonate (2.1 g, 15.2 mmol) and the mixture was stirred at reflux for 5 hours. The resulting mixture was concentrated and partitioned between ethyl acetate (3 times 30 mL) and water (100 mL). The combined ethyl acetate layers were dried over sodium sulphate, filtered and concentrated under vacuum. The crude product thus obtained was purified by column chromatography on silica gel (EtOAc: PE=1:20) to afford the title compound as a solid (2.5 g).

Workup

  1. temperatureat reflux for 5 hours
  2. concentrationThe resulting mixture was concentrated
  3. custompartitioned between ethyl acetate (3 times 30 mL) and water (100 mL)
  4. dry with materialThe combined ethyl acetate layers were dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe crude product thus obtained
  8. customwas purified by column chromatography on silica gel (EtOAc: PE=1:20)

Sources & evidence

ORD record
ord-07b206e39db242068ebf578b13b30372
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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