Benzyl Bromide → 4-Benzyloxy-2,6-bis(trifluoromethyl)nitrobenzene

HRID 1373733Notes

Reaction equation

HRID 1373733 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[N+:15]([C:18]1[C:23]([C:24]([F:27])([F:26])[F:25])=[CH:22][C:21]([OH:28])=[CH:20][C:19]=1[C:29]([F:32])([F:31])[F:30])([O-:17])=[O:16]>CC(C)=O>[CH2:7]([O:28][C:21]1[CH:20]=[C:19]([C:29]([F:32])([F:31])[F:30])[C:18]([N+:15]([O-:17])=[O:16])=[C:23]([C:24]([F:25])([F:26])[F:27])[CH:22]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 210756024-Nitro-3,5-bis(trifluoromethyl)phenol

Product 1

HCID 210756014-Benzyloxy-2,6-bis(trifluoromethyl)nitrobenzeneYield 94.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

Under ice cooling, potassium carbonate (7.23 g, 52.3 mmol) and benzyl bromide (5.45 mL, 45.8 mmol) were added to a solution of 4-nitro-3,5-bis(trifluoromethyl)phenol (12.0 g, 43.6 mmol) in acetone (250 mL). After stirring at 50° C. for 13 hours, the reaction mixture was filtered and the insoluble matter was washed with acetone. To the residue obtained by distilling the filtrate under reduced pressure, ethyl acetate and water were added to allow it to separate into layers. The aqueous layer was extracted twice with ethyl acetate. The organic layers were combined, washed successively with water and saturated saline, dried over anhydrous sodium sulfate, and distilled under reduced pressure to remove the solvent. The residue was recrystallized from hexane-acetone, whereby 15.0 g (yield: 94.3%) of 4-benzyloxy-2,6-bis(trifluoromethyl)nitrobenzene was obtained as pale yellow needle-like crystals.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthe insoluble matter was washed with acetone
  3. customTo the residue obtained
  4. distillationby distilling the filtrate under reduced pressure, ethyl acetate and water
  5. additionwere added
  6. customto separate into layers
  7. extractionThe aqueous layer was extracted twice with ethyl acetate
  8. washwashed successively with water and saturated saline
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationdistilled under reduced pressure
  11. customto remove the solvent
  12. customThe residue was recrystallized from hexane-acetone

Sources & evidence

ORD record
ord-babf878057564a04a33b2fc27644e624
Source dataset
uspto-grants-2007_01
Patent number
US07163944B2

Reaction notes

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