Nitric Acid → 5-Chloro-4-nitrothiophene-2-carbaldehyde

Temperature

-5 °C

5-Chlorothiophene-2-carbaldehyde (2.0 g, 13.6 mmol) was added dropwise to a stirred fuming nitric acid (13 mL) cooled to −5° C. with an ice/methanol bath. When addition was complete the stirred reaction mixture was allowed to warm slowly to 5° C. over 1 hour, then it was poured into ice/water (200 mL). The precipitated solid was collected by filtration, dissolved in dichloromethane (100 mL), washed with water and the organic layer was separated and dried (MgSO4). After filtration the solvent was removed under reduced pressure and the residual brown solid was crystallised from hexane (insoluble brown material was removed by decantation of the supernatant solution), to afford title product as an off-white solid (1.51 g, 58%). 1H NMR (300 MHz, CDCl3) δ: 9.83 (1H, s), 8.20 (1H, s).

1. additionWhen addition
2. customthe stirred reaction mixture
3. temperatureto warm slowly to 5° C. over 1 hour
4. filtrationThe precipitated solid was collected by filtration
5. dissolutiondissolved in dichloromethane (100 mL)
6. washwashed with water
7. customthe organic layer was separated
8. dry with materialdried (MgSO4)
9. filtrationAfter filtration the solvent
10. customwas removed under reduced pressure
11. customthe residual brown solid was crystallised from hexane (insoluble brown material
12. customwas removed by decantation of the supernatant solution),

ORD record

ord-0131aee8af204fabba77e0369bd5f634

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08680139B2