Benzyl Bromide → Dibenzyl-(2,4-difluoro-phenyl)-amine

HRID 45841Notes

Reaction equation

HRID 45841 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:3]=1[NH2:4].C(=O)([O-])[O-].[K+].[K+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([N:4]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:2]=1[F:1])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 97092,4-DifluoroanilineHCID 11430Potassium Carbonate

Product 1

HCID 58086650Dibenzyl-(2,4-difluoro-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,4-difluoroaniline (40.0 g, 0.31 mol) in N,N-dimethylformamide (400 mL) were added potassium carbonate (120 g, 0.92 mol, 3 eq) and benzyl bromide (112 mL, 0.71 mmol, 2.3 eq). The reaction was stirred with mechanical stirring at room temperature overnight. In order to quench the benzyl bromide in excess, NH4OH (90 mL) was added and the reaction was stirred overnight. The mixture was filtered and DMF was evaporated under reduced pressure. Ethyl acetate was added and the organic layer was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the oily crude was crystallized in methanol, obtaining after drying 71 g of dibenzyl-(2,4-difluoro-phenyl)-amine as a white solid (74%)

Workup

  1. stirringwith mechanical stirring at room temperature overnight
  2. customIn order to quench the benzyl bromide in excess, NH4OH (90 mL)
  3. additionwas added
  4. stirringthe reaction was stirred overnight
  5. filtrationThe mixture was filtered
  6. customDMF was evaporated under reduced pressure
  7. additionEthyl acetate was added
  8. washthe organic layer was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated under reduced pressure
  12. customthe oily crude was crystallized in methanol
  13. customobtaining
  14. dry with materialafter drying 71 g of dibenzyl-(2,4-difluoro-phenyl)-amine as a white solid (74%)

Sources & evidence

ORD record
ord-fb6ed139aa3e471cbaf5c3bdfadcf3c2
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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