Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butyl Acrylate | HCID 8846 | — |
| Reactant | 1-Bromo-2-methyl-4-nitrobenzene | HCID 251672 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Reactant | Sodium Acetate Trihydrate | HCID 23665404 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | N-methyl-2-pyrrolidone | HCID 13387 | — |
| Product | HCID 86644274 | HCID 86644274 | 86% |
Reaction Steps
A 0.28 mM palladium acetate solution (3.28 ml) was added to N-methylpyrrolidone (7 ml) solution of 2-bromo-5-nitrotoluene (1 g) and sodium acetate trihydrate (417 mg) in an argon atmosphere. The mixture was warmed to 120° C., and n-butyl acrylate (923 μl) was added thereto. The obtained mixture was stirred at 135° C. for 2 hours. A 0.28 mM palladium acetate solution (3.28 ml) and n-butyl acrylate (396 μl) were further added thereto, and the mixture was stirred for 4 hours. Subsequently, sodium acetate (265 mg) was added, and the mixture was further stirred for 1 hour. After the reaction was over, water (30 ml) was added to the resulting reaction mixture, and the mixture was separated with toluene and water. The organic layer was washed three times with water and once with a saturated sodium chloride solution, and then dried over anhydrous sodium sulfate. After the solvent was distilled off, the obtained residue was isolated and purified by silica gel column chromatography (n-hexane to ethyl acetate=8:1) to obtain Compound 5a (1.05 g, 86%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07855300B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-95fff439bbee4f868eed69082349cf50 |
|---|
| Source note | uspto-grants-2010_12 |
|---|