Sodium Iodide → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 2190482Notes

Reaction equation

HRID 2190482 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(C)=O>[CH2:12]([O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneYield 104.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-fluoro-2-nitrophenol (8.05 g, 51.2 mmol) in acetone (100 mL) were added benzyl bromide (8.90 g, 52.0 mmol), potassium carbonate (11.0 g, 79.3 mmol) and sodium iodide (1.51 g, 10.1 mmol) at room temperature, and the mixture was heated under reflux for 2.5 hr. The reaction mixture was cooled to room temperature, the inorganic salt was filtered off, and the filtrate was concentrated. The residue was dissolved in ethyl acetate (150 mL), and the mixture was washed with water (150 mL×2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (13.2 g) as a brown oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2.5 hr
  3. filtrationthe inorganic salt was filtered off
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  6. washthe mixture was washed with water (150 mL×2) and saturated brine (100 mL)
  7. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-82b7e558ea534399aeea46e986022777
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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