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

HRID 968668Notes

Reaction equation

HRID 968668 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]=[C:18]([OH:25])[CH:19]=[CH:20][C:21]=1[N+:22]([O-:24])=[O:23]>CN(C=O)C.CCOC(C)=O>[CH2:7]([O:25][C:18]1[CH:19]=[CH:20][C:21]([N+:22]([O-:24])=[O:23])=[C:16]([F:15])[CH:17]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

K2CO3 (8.97 g) and benzylbromide (4.25 mL) were added to a solution of 3-fluoro-4-nitrophenol (5.10 g) in anhydrous DMF (30 mL) at room temperature, and the mixture was stirred overnight. The mixture was diluted with EtOAc and washed with H2O and brine. The organic layer was dried over magnesium sulfate and concentrated. The residual solid was crystallized from EtOAc/hexane to yield 7.31 g of the title compound.

Workup

  1. washwashed with H2O and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residual solid was crystallized from EtOAc/hexane

Sources & evidence

ORD record
ord-4cfd45ca7fa6403b9fb60df1ac2da1b8
Source dataset
uspto-grants-2007_12
Patent number
US07304072B2

Reaction notes

Loading…