HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Iodobenzonitrile → 2-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Iodobenzonitrile | HCID 2759358 | — |
| Reactant | [5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane | HCID 11756135 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-[5-(Tert-butyldimethylsiloxymethyl)pyridin-2-yl]benzonitrile | HCID 9996395 | 68.6% |
Reaction Steps
A mixture of [5-(tert-Butyldimethylsilyloxymethyl)pyridin-2-yl]tri-n-butylstannane (11.5 g, 0.022 mol), 2-iodobenzonitrile (5.1 g, 0.022 mol), CuI (0.43 g, 0.002 mol), and bis(triphenylphosphine)palladium(II) chloride (0.80 g, 0.001 mol) in THF (40 mL) was heated under reflux for 48 h. The mixture was diluted with ether and washed with saturated aqueous NH4Cl, aqueous NH4OH, water, and brine, dried (MgSO4), and concentrated to give 4.9 g (67%) of product as a brown oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05149699 |
| Source dataset | uspto-grants-1992_09 |
| ORD ID | ord-495245b23c6441b5bc8a6b7d2ddf0078 |
| Source note | uspto-grants-1992_09 |