Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 5-Bromo-2-fluorobenzaldehyde | HCID 736327 | — |
| Reactant | HCID 22329086 | HCID 22329086 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22328906 | HCID 22328906 | 25.6% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06936602B1 |
|---|
| Source dataset | uspto-grants-2005_08 |
|---|
| ORD ID | ord-38a1d8439bdf4401aeaf9b4335a200b8 |
|---|
| Source note | uspto-grants-2005_08 |
|---|