반응 #2467980

반응 방정식

Sulfuric acid

nitric acid

thiophene-2-carboxylic acid

→

product

수율 75.0%

4-Nitrothiophene-2-carboxylic acid

수율 75.0%

반응 조건

후처리

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
   여과The precipitated solid was filtered
5. 5
   세척washed with cold water
6. 6
   기타dried
7. 7
   추출The filtrate was extracted with ethyl acetate
8. 8
   세척The combined ethyl acetate layer was washed with water, brine
9. 9
   건조dried over sodium sulfate
10. 10
    여과The solution was filtered
11. 11
    기타evaporated the solvent
12. 12
    workup.STIRRINGThe combined product was stirred with hexane (2×50 mL)
13. 13
    여과filtered the solid
14. 14
    기타dried

실험 절차

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.

출처