Benzaldehyde → N-Benzyl-2,4-difluoroaniline

HRID 1375772Notes

Reaction equation

HRID 1375772 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[F:7][C:8]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:9]=1[NH2:10].[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.B.[Na]>CO.C(O)(=O)C>[CH2:16]([NH:10][C:9]1[CH:11]=[CH:12][C:13]([F:15])=[CH:14][C:8]=1[F:7])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 97092,4-DifluoroanilineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 178418435HCID 178418435, compound

Product 1

HCID 22667090N-Benzyl-2,4-difluoroanilineYield 60%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

Magnesium sulfate (5.59 g) and a minor amount of acetic acid were added to a solution of 2,4-difluoroaniline (2.37 ml) and benzaldehyde (2.36 ml) in methanol (46 ml). The mixture was stirred at room temperature for 45 min. Sodium boron hydride (2.64 g) was added thereto under ice cooling, and the mixture was stirred at room temperature for one hr. The solvent was removed by distillation under the reduced pressure. Water and ethyl acetate were added to the residue. The mixture was stirred and was filtered through Celite. The organic layer was extracted with ethyl acetate and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure. The residue was purified by chromatography on silica gel by development with hexane/acetone (30/1) to give 3.04 g (yield 60%) of the title compound.

Workup

  1. stirringunder ice cooling, and the mixture was stirred at room temperature for one hr
  2. customThe solvent was removed by distillation under the reduced pressure
  3. additionWater and ethyl acetate were added to the residue
  4. stirringThe mixture was stirred
  5. filtrationwas filtered through Celite
  6. extractionThe organic layer was extracted with ethyl acetate
  7. dry with materialwas dried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation under the reduced pressure
  9. customThe residue was purified by chromatography on silica gel by development with hexane/acetone (30/1)

Sources & evidence

ORD record
ord-674be09be7104ba88fd764424b08679f
Source dataset
uspto-grants-2007_01
Patent number
US07169789B2

Reaction notes

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