Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Methyl Methacrylate | HCID 6658 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 1-Fluoro-3-[(4-iodophenoxy)methyl]benzene | HCID 22476621 | — |
| Catalyst | Tetrabutylammonium Bromide | HCID 74236 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 69288939 | HCID 69288939 | 42% |
Reaction Steps
A mixture of 1.2 g (3.7 mmol) of 1-(3-fluorobenzyloxy)-4-iodo-benzene, 2.06 g (14.9 mmol) of potassium carbonate and 1.70 g (52.8 mmol) of tetrabutyl ammonium bromide in 10 ml of dimethylformamide is treated under Ar with 48 mg (0.21 mmol) of palladium-(II)-acetate. 1.49 g (14.9 mmol) of methyl methacrylate is added and the mixture heated at 90° C. for about 40 min. The reaction mixture is poured into 150 ml dichloromethane, filtered and washed successively with 0.1 molar hydrochloric acid, saturated aqueous sodium hydrogencarbonate and water. The solution is dried over magnesium sulfate. Flash chromatography (silica gel, hexane/ethyl acetate 95:5) yields 461 mg (42%) of a colorless solid. MS: m/e=301.3 (M++H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06900354B2 |
|---|
| Source dataset | uspto-grants-2005_05 |
|---|
| ORD ID | ord-92939a72af04404f9c66fb0d34fcee2b |
|---|
| Source note | uspto-grants-2005_05 |
|---|