Реакция #562478

Уравнение реакции

2-bromo-1,3-dimethylbenzene

nitric acid

→

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

Выход 37.0%

Растворители

sulfuric acid

sulfuric acid

Условия реакции

Обработка

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice (200 g) the resulting solid
2. 2
   Фильтрацияfiltered
3. 3
   Промывкаwashed with water
4. 4
   Другоеdried in vacuo
5. 5
   ДругоеThe crude was purified by SiO2 chromatography
6. 6
   Промывкаeluting with petroleum ether/EtOAc (100:1)
7. 7
   Промывкаas eluting solvent

Методика

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).

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