Benzyl Bromide → 2-(Benzyloxy)-4-fluoro-1-nitrobenzene

HRID 430046Notes

Reaction equation

HRID 430046 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+]>C(#N)C>[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

5

Reactant 3

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

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

31.4 g of 5-fluoro-2-nitrophenol (0.2 mol) and 34.3 g of benzyl bromide (0.2 mol) are dissolved in 200 ml of dry acetonitrile in a 500 ml three-neck flask fitted with reflux condenser, stirrer and nitrogen inlet. 60 g of potassium carbonate (0.43 mol) are added, and the solution is refluxed for 2 hours in a temperature-controllable oil bath. The reaction solution is then allowed to cool to room temperature, and the residue is filtered off via a fluted filter. The resultant solution is then evaporated to half in a rotary evaporator and left to stand overnight at room temperature, during which the yellow-orange reaction product precipitates in crystalline form. The reaction product is then filtered off via a fluted filter, recrystallized from ethanol and then dried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum drying cabinet.

Workup

  1. customfitted
  2. temperaturewith reflux condenser, stirrer and nitrogen inlet
  3. temperaturethe solution is refluxed for 2 hours in a temperature-controllable oil bath
  4. filtrationthe residue is filtered off via
  5. filtrationa fluted filter
  6. customThe resultant solution is then evaporated to half in a rotary evaporator
  7. waitleft
  8. customthe yellow-orange reaction product precipitates in crystalline form
  9. filtrationThe reaction product is then filtered off via
  10. filtrationa fluted filter
  11. customrecrystallized from ethanol
  12. customdried for 48 hours under nitrogen at 40° C./10 mbar in a vacuum
  13. customdrying cabinet

Sources & evidence

ORD record
ord-b95ef843e0bb4905a88c99bb2a999ae8
Source dataset
uspto-grants-2001_11
Patent number
US06320081B1

Reaction notes

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