Benzyl Alcohol → 1-(Benzyloxy)-2,3-difluoro-4-nitrobenzene

HRID 2066288Notes

Reaction equation

HRID 2066288 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[F:12].[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:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[F:12])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 698711,2,3-Trifluoro-4-nitrobenzene

Product 1

HCID 574708771-(Benzyloxy)-2,3-difluoro-4-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1,2,3-trifluoro-4-nitrobenzene (5.0 g) and benzyl alcohol (2.92 ml) in N,N-dimethylformamide (20 ml) was added potassium carbonate (5.85 g), followed by stirring at room temperature for 62 hr and 45 min. To the reaction mixture was added water (80 ml) at 0° C., followed by stirring at 4° C. for 28 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 (6.54 g) which was a mixture of 2-(benzyloxy)-3,4-difluoro-1-nitrobenzene.

Workup

  1. stirringby stirring at 4° C. for 28 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-e49adba3747343c9b481900ab757f491
Source dataset
uspto-grants-2012_10
Patent number
US08288538B2

Reaction notes

Loading…