Benzyl Alcohol → 1-(Benzyloxy)-2,5-difluoro-4-nitrobenzene

HRID 1712656Notes

Reaction equation

HRID 1712656 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12](F)[C:11]([F:15])=[CH:10][C:9]=1[N+:16]([O-:18])=[O:17].[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[CH2:19]([O:26][C:12]1[CH:13]=[C:8]([F:7])[C:9]([N+:16]([O-:18])=[O:17])=[CH:10][C:11]=1[F:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 750121,2,4-Trifluoro-5-nitrobenzene

Product 1

HCID 574708681-(Benzyloxy)-2,5-difluoro-4-nitrobenzeneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (11.1 g) was added to a solution of 2,4,5-trifluoronitrobenzene (9.48 g) and benzyl alcohol (5.54 ml) in N,N-dimethylformamide (40 ml), followed by stirring at room temperature for 60 hours. Water (120 ml) was added to the reaction mixture at 0° C., followed by stirring at 4° C. for 24 hours. The precipitated crystals were collected by filtration, and washed with water. The crystals were dried under reduced pressure to give the title compound (11.5 g, 81%) as pale yellow crystals.

Workup

  1. stirringby stirring at 4° C. for 24 hours
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with water
  4. customThe crystals were dried under reduced pressure

Sources & evidence

ORD record
ord-b576a4048c64497187610f939331e106
Source dataset
uspto-grants-2010_09
Patent number
US07790885B2

Reaction notes

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