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

HRID 2265707Notes

Reaction equation

HRID 2265707 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-31c0bb57658e445caeada01ea7fadb29
Source dataset
uspto-grants-2010_12
Patent number
US07855290B2

Reaction notes

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