HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dimethylformamide → HCID 57804234, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Cyclopropylacetylene | HCID 138823 | — |
| Reactant | Methyl 4-Bromo-2-chlorobenzoate | HCID 22058730 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 57804234 | HCID 57804234 | 76% |
Reaction Steps
A mixture of methyl 4-bromo-2-chlorobenzoate (450 mg, 0.0018 mol), copper(I) iodide (34 mg, 0.00018 mol), 70% solution of cyclopropylacetylene (0.26 g, 0.0027 mol) in toluene and bis(triphenylphosphine)palladium(II) chloride (130 mg, 0.00018 mol) in Et3N (5 mL) and DMF (3 mL) was heated at 100° C. in a 50 mL sealed reaction vessel for 36 hours. After cooling, the mixture was filtered through Celite® and the filter cake was washed repeatedly with ethyl acetate. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give the product (320 mg, 76%) as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07576099B2 |
| Source dataset | uspto-grants-2009_08 |
| ORD ID | ord-f4f32a3c6fdf4147b820b6f773289a68 |
| Source note | uspto-grants-2009_08 |