HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Bromo-2-nitrobenzene → 4-(2-Nitrophenyl)but-3-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Bromo-2-nitrobenzene | HCID 11341 | — |
| Reactant | 3-Butyn-1-OL | HCID 13566 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 4-(2-Nitrophenyl)but-3-yn-1-ol | HCID 11745451 | 78.5% |
Reaction Steps
A solution of o-bromonitrobenzene (8.1 g, 0.04 mol) in 160 ml of triethylamine, under nitrogen, is treated sequentially with bis(triphenylphosphine)palladium(II)chloride (0.28 g, 0.4 mmol), 3-butyne-1-ol (2.81 g, 0.04 mol) and copper(I)iodide (0.15 g, 0.8 mmol), stirred for about 16 hours and filtered. The filtercake is washed with toluene. The filtrates are combined and concentrated in vacuo to give the title product as a dark oil, 6.0 g, 78.5% yield, identified by NMR and mass spectral analyses.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05856576 |
| Source dataset | uspto-grants-1999_01 |
| ORD ID | ord-828cf1896fe146b193c3ca0f64405f32 |
| Source note | uspto-grants-1999_01 |