HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → 2-{4-[3-(3,4-Dichlorophenyl)-propyl]phenylamino}benzoic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Methyl 2-bromobenzoate | HCID 11894 | — |
| Reactant | 4-[3-(3,4-Dichloro-phenyl)propyl]phenylamine | HCID 22269748 | — |
| Catalyst | Palladium | HCID 23938 | — |
| Catalyst | Di-p-tolylphosphino-1,1'-binaphthyl | HCID 18398271 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 2-{4-[3-(3,4-Dichlorophenyl)-propyl]phenylamino}benzoic acid methyl ester | HCID 54513625 | 82.6% |
Reaction Steps
The title compound was prepared from 4-[3-(3,4-dichlorophenyl)propyl]-phenylamine (600 mg, 2.14 mmol), 2-bromobenzoic acid methyl ester (380 mg, 1.78 mmol), cesium carbonate (812 mg, 2.49 mmol), tris(dibenzylideneacetone-dipaladium(0) (49 mg, 0.053 mmol) and (S)-2,2′-bis(di-p-tolylphosphino-1,1′-binaphthyl (98%, (S)-tol-BINAP) (54 mg, 0.080 mmol) (Ligand/Pd=1.5) in anhydrous toluene (15 mL) using the procedure described in Example 2, Step C. This procedure yielded an yellow oil, 0.61 g (1.47 mmol, 69%) of the desired product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06972287B1 |
| Source dataset | uspto-grants-2005_12 |
| ORD ID | ord-367032a5e3bc4740b90d24e15c1f2351 |
| Source note | uspto-grants-2005_12 |