HuagongsheHuagongshe Chemistry Print Report · For research reference only
Nitrogen → 3-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Methyl Acrylate | HCID 7294 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | (5-Fluoro-2-iodophenyl)(methyl)sulfane | HCID 58127007 | — |
| Catalyst | Tetrabutylammonium Chloride | HCID 70681 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-(4-Fluoro-2-methylsulfanyl-phenyl)-acrylic acid methyl ester | HCID 66922516 | 89% |
Reaction Steps
4-fluoro-1-iodo-2-methylsulfanyl-benzene (6.8 g 25.3 mmol), K2CO3 (9.9 g, 63.4 mmol), methyl acrylate (5.7 ml, 63.4 mmol), Tetra-n-butylammonium chloride (7.0 g, 25.3 mmol) and Pd(OAc)2 (1.1 g, 5.07 mmol) were mixed in DMF (150 ml). The mixture was heated at 50° C. under the atmosphere of N2 overnight, after which water was added and then extracted with ethyl acetate. The extracts were combined, washed with brine, dried over sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography to give the desired product (4.8 g, yield 89%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431581B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-a58fd78498504445a13fd200f17eda87 |
| Source note | uspto-grants-2013_04 |