HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → HCID 53840489, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | 4-(Trifluoromethyl)phenylboronic acid | HCID 2734389 | — |
| Reactant | Methyl 4-methoxy-2-(trifluoromethylsulfonyloxy)benzoate | HCID 10710352 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 53840489 | HCID 53840489 | 91.9% |
Reaction Steps
To a stirred solution of 4-methoxy-2-(trifluoro-methanesulfonyloxy)-benzoic acid methyl ester (6.28 g) in toluene (100 mL) was added LiCl (2.54 g) and Pd(PPh3)4 (1.15 g). After few minutes at room temperature, a 2M solution of Na2CO3 (26 mL) was added followed by a solution of 4-trifluoromethylphenyl boronic acid (4.17 g) in EtOH (30 mL). The resulting mixture was stirred under reflux for 6 hours. The mixture was cooled to room temperature and the phases were separated. The organic layer was then dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified by flash chromatography eluting with hexane/AcOEt (90/10) to give the title compound (5.7 g) as white crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06552022B1 |
| Source dataset | uspto-grants-2003_04 |
| ORD ID | ord-41dd6f3e84d0416aa32fd6f77b72f4ba |
| Source note | uspto-grants-2003_04 |