反応 #562478

反応方程式

2-bromo-1,3-dimethylbenzene

nitric acid

→

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

収率 37.0%

溶媒

sulfuric acid

sulfuric acid

反応条件

後処理

1. 1
   workup.ADDITIONThe reaction mixture was poured onto ice (200 g) the resulting solid
2. 2
   ろ過filtered
3. 3
   洗浄washed with water
4. 4
   その他dried in vacuo
5. 5
   その他The crude was purified by SiO2 chromatography
6. 6
   洗浄eluting with petroleum ether/EtOAc (100:1)
7. 7
   洗浄as eluting solvent

実験手順

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).

出典