Nitric Acid → 757251-37-9
Reaktionsgleichung
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[OH:9].[N+:10]([O-])([OH:12])=[O:11]>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[CH:5]=[C:4]([F:8])[C:3]=1[OH:9]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 15 °C
Versuchsvorschrift
A solution of 2-chloro-6-fluorophenol (1.0 g, 6.82 mmol) in concentrated acetic acid (3.0 mL) was cooled to 0° C. Fuming nitric acid (559 mg, 8.87 mmol) was added dropwise, maintaining the reaction temperature between 10 to 20° C. The reaction was allowed to stir at 0° C. for 3 h. The mixture was poured over ice and was allowed to warm to room temperature. The aqueous was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (1×50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude red solid was purified using the Biotage Quad 4 (25 M column) eluting with 9:1 Hexanes/EtOAc to afford the title compound as a yellow solid (326 mg, 1.70 mmol; 25% yield). 1H-NMR (DMSO-d6) δ 11.74 to 12.77 (broad s, 1H), 8.10 to 8.16 (m, 2H).