HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 19770Generated: October 26, 2026
Dimethylformamide → 4-(Pentafluoroethyl)benzonitrile
https://huagongshe.com/reaction/19770
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 4-Iodobenzonitrile | HCID 76467 | — |
| Reactant | Sodium pentafluoropropionate | HCID 2733305 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | 4-(Pentafluoroethyl)benzonitrile | HCID 14774185 | 52.3% |
Reaction Steps
A mixture of 4-iodobenzonitrile (10.0 g, 43.7 mmol), sodium pentafluoroproprionate (15.4 g, 82.9 mmol), and copper(I) iodide (16.6 g, 87.3 mmol), DMF (160 mL), and toluene (60 mL) was heated at 160° C. for 16 h, allowing most of the toluene to distil off. After cooling, ethyl acetate (200 mL) was added, and the mixture was filtered through diatomaceous earth, and the filtrate was partitioned between ethyl acetate/heptane and water. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (5.05 g 52%). Yellow oil, MS (EI) 221.1 (M+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07745477B2 |
|---|
| Source dataset | uspto-grants-2010_06 |
|---|
| ORD ID | ord-ffd08d2350414257bcb2b75fcce9e152 |
|---|
| Source note | uspto-grants-2010_06 |
|---|
