Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Potassium Iodide | HCID 4875 | — |
| Reactant | HCID 21107090 | HCID 21107090 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 21107101 | HCID 21107101 | 88.5% |
Reaction Steps
A suspension of 5-bromo-7-methoxy-3-(4-methoxyphenyl)-4-oxo-4H-1-benzopyran (95 mg), copper(I) iodide (250 mg) and potassium iodide (462 mg) in DMSO (6 mL) was heated at 115° C. for 2 h. The mixture was cooled, poured into 1M hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with 1M hydrochloric acid and brine and dried over MgSO4. Chromatography on silica gel (eluant: ethyl acetate-dichloromethane-hexane 1:10:20) afforded the title compound (95 mg). 1H NMR (DMSO-d6): 8.40 (s, 1H), 7.63 (d, 1H, J=2.7 Hz), 7.47 (d, 2H, J=8.7 Hz), 7.22 (d, 1H, J=2.7 Hz), 6.99 (d, 2H, J=8.7 Hz), 3.90 (s, 3H), 3.79 (s, 3H); MS: 409 (MH+); HPLC tR: 2.83 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07226945B2 |
|---|
| Source dataset | uspto-grants-2007_06 |
|---|
| ORD ID | ord-8d802a4500fd426ab489364b4becf9ca |
|---|
| Source note | uspto-grants-2007_06 |
|---|
