HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 4-Chlorophenylboronic acid | HCID 74299 | — |
| Reactant | Methyl 4-bromo-5-(2,4-dichlorophenyl)-3-methoxythio-phene-2-carboxylate | HCID 67502528 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | Methyl 4-(4-chlorophenyl)-5-(2,4-dichlorophenyl)-3-methoxythiophene-2-carboxylate | HCID 67495513 | 75.6% |
Reaction Steps
7.75 g of (4-chlorophenyl)boronic acid and then, dropwise, 40.93 ml of a 2M solution of Na2CO3 are added to a solution of 16.21 g of the compound of step B) in 110 ml of toluene. Argon is sparged into the reaction mixture for 30 minutes, then 2.36 g of Tetrakis are added and heating is carried out at 110° C. for 18 hours. After cooling to AT, the reaction mixture is rinsed with 80 ml of distilled water, then extraction is carried out with 80 ml of EtOAc, drying is carried out over Na2SO4, and the solvent is evaporated off under vacuum. The reaction crude is purified by silica gel chromatography, elution being carried out with heptane and then with a heptane/EtOAc mixture (85/15; v/v). 13.23 g of the expected compound are obtained.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08486971B2 |
| Source dataset | uspto-grants-2013_07 |
| ORD ID | ord-16b580ed79724cb39d1800511ed3c0e2 |
| Source note | uspto-grants-2013_07 |