Nitric Acid → 1-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

Temperature

-5 °C

2-Chloro-5-acetylthiophene (80.3 g, 0.5 mol) was added in portions to fuming nitric acid (500 mL) cooled to −5° C. with an ice/methanol bath. On completion of addition the reaction was removed from the cold bath and stirred at ambient temperature for 30 minutes before the reaction mixture was poured into ice water (4 L). After stirring for 10 minutes the solid which formed was collected by filtration and washed with water (500 mL). The solid was then dissolved in dichloromethane (500 mL) the water was separated and the organic solution was dried (MgSO4). Removal of the solvent under reduced pressure gave an orange solid. The crude material was re-crystallized from IMS (350 mL) to give the title product as a light brown solid (46.89 g, 45% yield). 1H NMR (CDCl3) δ: 8.07 (1H, s), 2.58 (3H, s).

1. additionOn completion of addition the reaction
2. customwas removed from the cold bath
3. additionwas poured into ice water (4 L)
4. stirringAfter stirring for 10 minutes the solid which
5. customformed
6. filtrationwas collected by filtration
7. washwashed with water (500 mL)
8. dissolutionThe solid was then dissolved in dichloromethane (500 mL) the water
9. customwas separated
10. dry with materialthe organic solution was dried (MgSO4)
11. customRemoval of the solvent under reduced pressure
12. customgave an orange solid
13. customThe crude material was re-crystallized from IMS (350 mL)

ORD record

ord-2c7addcda28c415dab146b159aeeff45

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680139B2