HuagongsheHuagongshe Chemistry Print Report · For research reference only
Hydrochloric Acid → {2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzene, 1-iodo-4-(trifluoromethyl)- | HCID 67993 | — |
| Reactant | (2-Methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester | HCID 86602538 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | {2-Methyl-4-[3-(4-trifluoromethyl-phenyl)-prop-2-ynylsulfanyl]-phenoxy}-acetic acid tert-butyl ester | HCID 69458063 | 52.8% |
Reaction Steps
A degassed (argon) solution of 96.0 mg (0.33 mmol) (2-methyl-4-prop-2-ynylsulfanyl-phenoxy)-acetic acid tert-butyl ester, 0.053 ml (0.36 mmol) 1-iodo-4-trifluoromethyl-benzene and 0.086 (0.621 mmol) Et3N in 1 ml DMF was treated with 37.9 mg (0.03 mmol) Pd(PPh3)4 and 12.5 mg (0.07 mmol) of CuI. After stirring for 2 h at room temperature, the reaction was distributed between 1N HCl and ether (three times). Washing of the organic layer with saturated aqueous NH4Cl solution and brine, drying (Na2SO4) and evaporation of the solvents, followed by flash chromatography (SiO2, n-heptane/EtOAc 1 to 5%), yielded 76 mg of the title compound as yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07253192B2 |
| Source dataset | uspto-grants-2007_08 |
| ORD ID | ord-b304c27d0097490cb727dbc9e1390786 |
| Source note | uspto-grants-2007_08 |