Dimethylformamide → Dibenzyl-(2,4-difluoro-phenyl)-amine

HRID 38102Notes

Reaction equation

HRID 38102 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH2:9].CN(C)C=O.[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([N:9]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:3]1[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=1[F:1])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 97092,4-Difluoroaniline

Product 1

HCID 58086650Dibenzyl-(2,4-difluoro-phenyl)-amineYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2,4-difluoro-phenylamine (a, 2.0 g, 15.5 mmol) in N,N-dimethylformamide (20 mL) potassium carbonate (6.0 g, 45 mmol) and benzyl bromide (5.49 mL, 35 mmol) were added. The reaction was stirred at room temperature overnight. The reaction was poured into water and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and purified by silica gel column chromatography eluting with hexane to give dibenzyl-(2,4-difluoro-phenyl)-amine as colourless oil (4.34 g, 90%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by silica gel column chromatography
  7. washeluting with hexane

Sources & evidence

ORD record
ord-8b88a8896a624baaa7d77a3f19871ca1
Source dataset
uspto-grants-2013_09
Patent number
US08524707B2

Reaction notes

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