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

HRID 388513Notes

Reaction equation

HRID 388513 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), and the mixture was stirred at room temperature for 60 hours. Water (120 ml) was added to the reaction mixture at 0° C. and the mixture was stirred 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. stirringthe mixture was stirred 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-2020f9cdc25e4430adc7b4d05e786da9
Source dataset
uspto-grants-2013_02
Patent number
US08377938B2

Reaction notes

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