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

HRID 2066277Notes

Reaction equation

HRID 2066277 reaction equation
[F:1][C:2]1[CH:7]=[C:6](F)[C:5]([F:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH2:13]([O:20][C:6]1[CH:7]=[C:2]([F:1])[C:3]([N+:10]([O-:12])=[O:11])=[CH:4][C:5]=1[F:9])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=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

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

Workup

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

Sources & evidence

ORD record
ord-52585a00972540f2b6116bab2e345844
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

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