Water → 4-Benzyloxy-2-fluoro-1-nitrobenzene

HRID 576063Notes

Reaction equation

HRID 576063 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[F:16][C:17]1[CH:18]=[C:19]([OH:26])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24]>CN(C)C=O>[CH2:1]([O:26][C:19]1[CH:20]=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([F:16])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 5209483-Fluoro-4-nitrophenol

Product 1

HCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (70 mL), 3-fluoro-4-nitrophenol was dissolved, and benzyl bromide (6.53 g, 38.2 mmol) and potassium carbonate (6.59 g, 47.7 mmol) were added thereto and the mixture was stirred at room temperature for 18 hr. Water (100 mL) was added to the reaction mixture and the mixture was extracted three times with ethyl acetate (100 mL). The combined organic layer was washed with 1 mol/L hydrochloric acid and brine. The mixture was dried over anhydrous magnesium sulfate and filtered, and the solvent was distilled off under reduced pressure. The resulting solid was washed with hexane to afford 4-(benzyloxy)-2-fluoro-1-nitrobenzene as a yellow solid (7.47 g).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate (100 mL)
  2. washThe combined organic layer was washed with 1 mol/L hydrochloric acid and brine
  3. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off under reduced pressure
  6. washThe resulting solid was washed with hexane

Sources & evidence

ORD record
ord-24c54020a11b4d1f823e8ef73ea8ec01
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

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