Reaktionsgleichung
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]Komponenten
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 85 °C
Versuchsvorschrift
To a solution of 4-methyl-3-nitroanisole (16.53 mL; 119.64 mmol; 1 eq), in CCl4 (500 mL) is added N-bromosuccinimide (21.29 g; 119.64 mmol; 1 eq) and azoisobutyronitrile (392.9 mg; 2.39 mmol; 0.02 eq). The mixture is heated at 85° C. for 20 h. The solution is cooled down to room temperature and the precipitate of succinimide is removed by filtration. The filtrate is concentrated to afford a yellow oil. The oil crystallizes after one night at −25° C. It is redissolved in EtOAc (15 mL) and petroleum ether is added. After 2 h at −25° C., the compound recrystallizes. After filtration and washing with petroleum ether, the solid is dried under vacuum to afford 17.4 g (59%) of the title compound as a liquid. 1H NMR (DMSO-d6) δ 7.68 (d, J=8 Hz, 1H), 7.56 (d, J=3 Hz, 1H), 7.33 (dd, J=8.0, 3.0 Hz, 1H), 4.89 (s, 2H), 3.87 (s, 3H). HPLC (max plot) 99%; Rt 4.09 min.
Aufarbeitung
- temperatureThe solution is cooled down to room temperature
- customthe precipitate of succinimide is removed by filtration
- concentrationThe filtrate is concentrated
- customto afford a yellow oil
- customThe oil crystallizes after one night at −25° C
- dissolutionIt is redissolved in EtOAc (15 mL)
- additionpetroleum ether is added
- customthe compound recrystallizes
- filtrationAfter filtration
- washwashing with petroleum ether
- customthe solid is dried under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-f239c2fc4bd14fdf83b92f423f9a9511
- Quelldatensatz
- uspto-grants-2013_12
- Patentnummer
- US08614215B2
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