Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Propyne | HCID 6335 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 4-Bromo-2-benzofuran-1,3-dione | HCID 350255 | — |
| Catalyst | Triphenylphosphine | HCID 11776 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 4-(1-Propynyl)phthalic Anhydride | HCID 21339433 | 98% |
Reaction Steps
Bromophtalic anhydride (50.0 g, 0.22 mol), triethylamine (33.8 mL, 0.24 mol) and toluene (220 mL) were mixed in a glass reactor over nitrogen (g) atmosphere at room temperature. Bis(triphenylphosphine)palladiumchloride (0.77 g, 0.001 mol), CuI (0.42 g, 0.002 mol) and triphenylphosphine (0.87 g, 0.003 mol) were added and the temperature was raised to 50° C. Propyne (18.0 g, 0.45 mol) was slowly added through a gas inlet during 3 hours. The reaction mixture was filtered through a glass filter funnel and the solution was concentrated to dryness to give crude solid product (40.1 g, 98%). The product was re-crystallized from toluene to give a light yellow solid (24.7 g, 60%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08772418B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-2b038663f3084b99aee39161d65e8bfa |
|---|
| Source note | uspto-grants-2014_07 |
|---|
