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

HRID 392809Notes

Reaction equation

HRID 392809 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-b75306af8a934e40b8eb09a37908ee91
Source dataset
uspto-grants-2004_10
Patent number
US06803372B2

Reaction notes

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