HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Chloride → 4-(2-Fluoro-4-nitrophenyl)butanenitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Chloride | HCID 5234 | — |
| Reactant | Methyl 4-cyano-2-(2-fluoro-4-nitrophenyl)butanoate | HCID 68292723 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-(2-Fluoro-4-nitrophenyl)butanenitrile | HCID 57672625 | 170.8% |
Reaction Conditions
| Temperature | 160 °C |
|---|
Reaction Steps
A mixture of compound 66 (1.2 g, 4.5 mmol), NaCl (0.8 g, 13.5 mmol) and water (1.4 mL) in DMSO (30 mL) was stirred at 160° C. for 24 h under N2. After cooling, the mixture was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified with silica gel column chromatography (PE:EtOAc=5:1) to give the compound 67 (1.6 g, 43%) as a yellow oil. 1H NMR (400 MHz, CDCl3) δ7.99-8.04 (m, 1H), 7.91-7.96 (m, 1H), 7.38-7.44 (m, 1H), 2.93 (t, 2H, J=7.5 Hz), 2.41 (t, 2H, J=7.0 Hz), 1.98-2.07 (m, 2H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09216957B2 |
| Source dataset | uspto-grants-2015_12 |
| ORD ID | ord-7a3ce36ea6b747f7a728def0e7405ad0 |
| Source note | uspto-grants-2015_12 |