Water → HCID 22328906, compound

HRID 587047Notes

Reaction equation

HRID 587047 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH3:2].[Br:17][C:18]1[CH:19]=[CH:20][C:21](F)=[C:22]([CH:25]=1)[CH:23]=[O:24].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[Br:17][C:18]1[CH:19]=[CH:20][C:21]([N:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:7][CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])=[C:22]([CH:23]=[O:24])[CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7363275-Bromo-2-fluorobenzaldehydeHCID 22329086HCID 22329086, compound

Product 1

HCID 22328906HCID 22328906, compoundYield 25.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In DMF (43.9 ml) was dissolved tert-butyl 4-[(2-ethoxyethyl)amino]butyrate (5.5 g). To the solution was added 5-bromo-2-fluorobenzaldehyde (4.4 g), followed by addition of potassium carbonate (3.6 g). The mixture was stirred at 90° C. for 60 hours and cooled to room temperature. The reaction solution was added to water, the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. The solvent was removed under reduced pressure, and the resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=6/1→5/1) to give tert-butyl 4-(4-bromo(2-ethoxyethyl)-2-formylanilino]butyrate (2.3 g).

Workup

  1. temperaturecooled to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried with magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting residue was purified with silica gel column chromatography (hexane/ethyl acetate=6/1→5/1)

Sources & evidence

ORD record
ord-38a1d8439bdf4401aeaf9b4335a200b8
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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