Reaktion #562478

Reaktionsgleichung

2-bromo-1,3-dimethylbenzene

nitric acid

→

2-bromo-1,3-dimethyl-4-nitrobenzene

Ausbeute 37.0%

Lösungsmittel

sulfuric acid

sulfuric acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice (200 g) the resulting solid
2. 2
   Filtrationfiltered
3. 3
   Waschenwashed with water
4. 4
   Sonstigedried in vacuo
5. 5
   SonstigeThe crude was purified by SiO2 chromatography
6. 6
   Wascheneluting with petroleum ether/EtOAc (100:1)
7. 7
   Waschenas eluting solvent

Vorschrift

To a mixture of 2-bromo-1,3-dimethylbenzene (5.0 g, 27.03 mmol) in sulfuric acid (98%, 40 mL) at −10° C. was added dropwise a solution of nitric acid (68%, 2.74 g, 27.03 mmol) in sulfuric acid (98%, 10 mL). After the reaction was complete the mixture was stirred at −10° C. for 1 h. The reaction mixture was poured onto ice (200 g) the resulting solid filtered, washed with water, and dried in vacuo. The crude was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (100:1) as eluting solvent to afford 2.3 g (37%) of 2-bromo-1,3-dimethyl-4-nitrobenzene as yellow solid (298): 1H NMR (500 MHz, DMSO-d6): δ 7.79 (d, J=8.5, 1H), 7.43 (d, J=8.5, 1H), 2.47 (s, 3H), 2.44 (s, 3H).

Quelle