2,4-Difluoroaniline → 4-bromo-N-(2,4-difluorophenyl)butanamide

HRID 2416951Notes

Reaction equation

HRID 2416951 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:29]=[C:28]([F:30])[CH:27]=[CH:26][C:24]=1[NH2:25].[Br:31][CH2:32][CH2:33][CH2:34][C:35](O)=[O:36]>CN(C=O)C>[Br:31][CH2:32][CH2:33][CH2:34][C:35]([NH:25][C:24]1[CH:26]=[CH:27][C:28]([F:30])=[CH:29][C:23]=1[F:22])=[O:36]

Participants

6

Reactant 4

HCID 97092,4-DifluoroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 758094-Bromobutyric acid

Product 1

HCID 226335314-bromo-N-(2,4-difluorophenyl)butanamideYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

WSC (2.1 g, 11 mmols) and HOBt (1.49 g, 11 mmols) were added to a DMF (30 ml) solution of 2,4-difluoroaniline (1.29 g, 10 mmols) and 4-bromobutyric acid (2.5 g, 15 mmols), and stirred at room temperature for 12 hours. The reaction mixture was extracted with ether. The organic layer was washed with water 1 N HCl, an aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate, and the solvent was evaporated. Then, the residue was purified through preparative thin-layer chromatography (developer:hexane/acetone=5/1), and the resulting crystals were recrystallized from ether-hexane to obtain 1.6 g (yield: 58%) of 4-bromo-N-(2,4-difluorophenyl)butanamide as colorless needle-like crystals.

Workup

  1. extractionThe reaction mixture was extracted with ether
  2. washThe organic layer was washed with water 1 N HCl
  3. dry with materialan aqueous saturated solution of sodium hydrogencarbonate and saturated saline in that order, and dried with anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThen, the residue was purified through preparative thin-layer chromatography (developer:hexane/acetone=5/1)
  6. customthe resulting crystals were recrystallized from ether-hexane

Sources & evidence

ORD record
ord-b62791565c424893b8317f26391ad3a3
Source dataset
uspto-grants-2004_11
Patent number
US06825223B2

Reaction notes

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