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

HRID 576061Notes

Reaction equation

HRID 576061 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.[F:15][C:16]1[CH:17]=[CH:18][C:19]([N+:23]([O-:25])=[O:24])=[C:20]([OH:22])[CH:21]=1.O>CN(C)C=O>[CH2:7]([O:22][C:20]1[CH:21]=[C:16]([F:15])[CH:17]=[CH:18][C:19]=1[N+:23]([O-:25])=[O:24])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 99375-Fluoro-2-nitrophenolHCID 11430Potassium Carbonate

Product 1

HCID 110969082-(Benzyloxy)-4-fluoro-1-nitrobenzeneYield 111.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.07 g, 15.0 mmol) and benzyl bromide (1.43 mL, 12.0 mmol) were added to a solution of 5-fluoro-2-nitrophenol (1.57 g, 10.0 mmol) in N,N-dimethylformamide (30 mL) at room temperature and the mixture was stirred for 2 hr. Water was added to the reaction mixture and the mixture was extracted three times with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid and brine and dried over anhydrous magnesium sulfate and then the desiccant was filtered off, followed by concentration under reduced pressure. The resulting residue was dried under reduced pressure to afford 2-(benzyloxy)-4-fluoro-1-nitrobenzene as a pale yellow oil (2.76 g).

Workup

  1. extractionthe mixture was extracted three times with ethyl acetate
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe desiccant was filtered off
  5. concentrationfollowed by concentration under reduced pressure
  6. customThe resulting residue was dried under reduced pressure

Sources & evidence

ORD record
ord-8bb6cb199341466d9361d2555471ce29
Source dataset
uspto-grants-2015_05
Patent number
US09035059B2

Reaction notes

Loading…