反応 #2467980

反応方程式

Sulfuric acid

nitric acid

thiophene-2-carboxylic acid

→

product

収率 75.0%

4-Nitrothiophene-2-carboxylic acid

収率 75.0%

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the above nitration mixture slowly for 15 min at the same temperature
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice cold water
3. 3
   workup.STIRRINGstirred for 30 min
4. 4
   ろ過The precipitated solid was filtered
5. 5
   洗浄washed with cold water
6. 6
   その他dried
7. 7
   抽出The filtrate was extracted with ethyl acetate
8. 8
   洗浄The combined ethyl acetate layer was washed with water, brine
9. 9
   乾燥dried over sodium sulfate
10. 10
    ろ過The solution was filtered
11. 11
    その他evaporated the solvent
12. 12
    workup.STIRRINGThe combined product was stirred with hexane (2×50 mL)
13. 13
    ろ過filtered the solid
14. 14
    その他dried

実験手順

Sulfuric acid (3.0 mL, 5.505 g, 56.17 mmol) was added to nitric acid (2.0 mL, 2.98 g, 49.6 mmol) slowly at 0-10° C. After completion of the addition, thiophene-2-carboxylic acid (2.8 g, 21.87 mmol) was added to the above nitration mixture slowly for 15 min at the same temperature and stirred the mixture for 1 h. The reaction mixture was poured into ice cold water and stirred for 30 min. The precipitated solid was filtered, washed with cold water and dried. The filtrate was extracted with ethyl acetate. The combined ethyl acetate layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and evaporated the solvent. The combined product was stirred with hexane (2×50 mL) and filtered the solid and dried to give the product as an off-white solid (2.8 g, 75%), mp 110-118° C. The product was a mixture of two compounds by HPLC and 1H NMR and was proceeded to the next step.

出典